N-(1,2,5-Oxadiazol-3-yl)-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)bicycloarylcarboxamides and their use as herbicides

ABSTRACT

N-(1,2,5-Oxadiazol-3-yl)-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)bicycloarylcarboxamides of the general formula (I) are described as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I), R 3 , R 4  and R 5  are each radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q is a heterocycle. X and Y are each oxygen and sulfur.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a §371 National Stage Application ofPCT/EP2012/054269, filed Mar. 12, 2012, which claims priority toEuropean Application No. 11158258.1, filed Mar. 15, 2011.

BACKGROUND OF THE INVENTION

1. Field of the Invention

2. Description of Related Art

The invention relates to the technical field of herbicides, especiallythat of herbicides for selective control of broad-leaved weeds and weedgrasses in crops of useful plants.

WO2003/010143 and WO2003/010153 disclose particular N-(tetrazol-5-yl)-and N-(triazol-5-yl)benzamides and the pharmacological action thereof.Under CAS No. 639048-78-5, the compoundN-(1-propyltetrazol-5-yl)-2,5-dichlorobenzamide is known. No herbicidalaction of these compounds is disclosed in these documents. Europeanpatent applications No. 0912169.0 and No. 10174893.7, which have earlierpriority dates but were yet to be published at the priority date of thepresent application, disclose N-(1,2,5-oxadiazol-3-yl)-,N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides and the usethereof as herbicides.

SUMMARY

It has now been found that N-(1,2,5-oxadiazol-3-yl)-, N-(tetrazol-5-yl)-and N-(triazol-5-yl)bicycloarylcarboxamides are of good suitability asherbicides.

The present invention thus provides N-(1,2,5-oxadiazol-3-yl)-,N-(tetrazol-5-yl)- or N-(triazol-5-yl)bicycloarylcarboxamides of theformula (I) or salts thereof

in which

-   Q is a Q1, Q2 or Q3 radical,

-   R¹ is (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,    halo-(C₂-C₆)-alkynyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₂-C₆)-alkenyl, (C₁-C₆)-alkoxy-(C₂-C₆)-alkynyl,    CH₂R⁶, heteroaryl, heterocyclyl or phenyl, where the three latter    radicals are each substituted by u radicals from the group    consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,    halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkylthio,    (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy,    halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl;-   R² is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,    halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,    (C₂-C₆)-alkenyl, (C₂-C₆)-alkenyloxy, halo-(C₂-C₆)-alkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy, halo-(C₂-C₆)-alkynyl, cyano,    nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino,    benzoylamino, methoxycarbonyl, ethoxycarbonyl,    methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl,    methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl,    halogen, amino, aminocarbonyl, methylaminocarbonyl,    dimethylaminocarbonyl, methoxymethyl, or heteroaryl, heterocyclyl or    phenyl each substituted by u radicals from the group consisting of    methyl, ethyl, methoxy, trifluoromethyl and halogen;-   R³ and R⁴ are each independently hydrogen, (C₁-C₆)-alkyl,    halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,    (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl,    (C₃-C₇)-halocycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,    (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen,    nitro or cyano;-   R⁵ is hydrogen or fluorine;-   R⁶ is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido,    N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl,    methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl,    trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl,    dimethylaminocarbonyl, (C₃-C₆)-cycloalkyl, or heteroaryl,    heterocyclyl or phenyl each substituted by u radicals from the group    consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen;-   R⁷ and R⁸ are each independently hydrogen, (C₁-C₆)-alkyl,    halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,    (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl,    halo-(C₃-C₇)-cycloalkyl, —OR⁹, S(O)_(m)R⁹, (C₁-C₆)-alkylthio,    halo-(C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl,    halo-(C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl,    halo-(C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen,    nitro, cyano, heteroaryl, heterocyclyl or phenyl, where the three    latter radicals are each substituted by u radicals from the group    consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,    halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkylthio,    (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy,    halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,    or-   R⁷ and R⁸ together with the carbon atom to which they are bonded    form the —X¹—(CH₂)_(r)—X²—, —(CH₂)_(s)—X³—, —(CH₂)_(t)—X³—CH₂—,    —(CH₂)_(v)—X³—CH₂CH₂— or —(CH₂)_(w)— unit in which each of the (CH₂)    groups is substituted by m radicals from the group consisting of    halogen, methyl and (C₁-C₃)-alkoxy,    or-   R⁷ and R⁸ together with the carbon atom to which they are bonded    form the —O—N((C₁-C₃)-alkyl)-CHR¹⁰—CH₂— or —O—N═CR¹⁰—CH₂— unit in    which each of the (CH₂) groups is substituted by m radicals from the    group consisting of halogen and methyl;-   R⁹ is hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,    (C₃-C₇)-cycloalkyl, (C₃-C₇)-halocycloalkyl,    (C₃-C₇)-cycloalkyl-(C₁-C₃)-alkyl,    halo-(C₃-C₇)-cycloalkyl-(C₁-C₃)-alkyl, heteroaryl, heterocyclyl or    phenyl, where the three latter radicals are each substituted by s    radicals from the group consisting of halogen, nitro, cyano,    (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,    (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and    (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl;-   R¹⁰ is hydrogen, (C₁-C₃)-alkyl, or phenyl substituted by u radicals    from the group consisting of (C₁-C₃)-alkyl, halogen, cyano and    nitro;-   R¹¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,    formyl, (C₂-C₆)-alkylcarbonyl, (C₂-C₆)-alkoxycarbonyl or    (C₁-C₂)-alkylsulfonyl;-   X and Y are each independently O, S, SO, SO₂, C═O, C═S, NR¹⁰, CR⁷R⁸,    C═NOR¹⁰ or C═NN(R¹¹)₂;-   X¹ and X² are each independently O, S or N((C₁-C₃)-alkyl);-   X³ is O or S;-   m is 0, 1 or 2;-   n is 1, 2 or 3;-   r is 2, 3 or 4;-   s is 2, 3, 4 or 5;-   t is 1, 2, 3 or 4;-   u is 0, 1, 2 or 3;-   v is 2 or 3;-   w is 2, 3, 4, 5 or 6.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

In the formula (I) and all the formulae which follow, alkyl radicalshaving more than two carbon atoms may be straight-chain or branched.Alkyl radicals are, for example, methyl, ethyl, n- or isopropyl, n-,iso-, tert- or 2-butyl, pentyls, hexyls such as n-hexyl, isohexyl and1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, semisaturated or fully unsaturated cyclicradical containing 3 to 6 ring atoms, of which 1 to 4 are from the groupof oxygen, nitrogen and sulfur, and which may additionally be fused by abenzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl,tetrahydrofuranyl, dihydrofuranyl and oxetanyl,

Heteroaryl is an aromatic cyclic radical containing 3 to 6 ring atoms,of which 1 to 4 are from the group of oxygen, nitrogen and sulfur, andwhich may additionally be fused by a benzo ring. For example, heteroarylis benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl,oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl,benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl,1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl,2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl,1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

When a group is polysubstituted by radicals, this means that this groupis substituted by one or more identical or different radicals from thosementioned.

According to the nature and the bonding of the substituents, thecompounds of the general formula (I) may be present as stereoisomers.When, for example, one or more asymmetric carbon atoms are present,enantiomers and diastereomers may occur. Stereoisomers likewise occurwhen n is 1 (sulfoxides). Stereoisomers can be obtained from themixtures obtained in the preparation by customary separation methods,for example by chromatographic separation processes. It is equallypossible to selectively prepare stereoisomers by using stereoselectivereactions using optically active starting materials and/or auxiliaries.The invention also relates to all stereoisomers and mixtures thereofwhich are encompassed by the general formula (I) but not definedspecifically.

Preference is given to compounds of the general formula (I) in which

-   R¹ is (C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, halo-(C₁-C₃)-alkyl or    (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl;-   R² is hydrogen, (C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl,    halo-(C₁-C₃)-alkyl, (C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy, cyano,    nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino,    methoxycarbonyl, ethoxycarbonyl, halogen, amino, aminocarbonyl,    methylaminocarbonyl, dimethylaminocarbonyl or methoxymethyl;-   R³ and R⁴ are each independently hydrogen, (C₁-C₃)-alkyl,    halo-(C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, (C₁-C₃)-alkoxy,    (C₁-C₃)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro    or cyano;-   R⁵ is hydrogen;-   R⁷ and R⁸ are each independently hydrogen, (C₁-C₃)-alkyl,    halo-(C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, —OR⁹, —S(O)_(m)R⁹,    (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl, (C₁-C₃)-alkylsulfonyl,    (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl, halogen, nitro, cyano, heteroaryl,    heterocyclyl or phenyl, where the three latter radicals are each    substituted by u radicals from the group consisting of halogen,    nitro, cyano, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl,    (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl, (C₁-C₃)-alkylsulfonyl,    (C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy and    (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl,    or-   R⁷ and R⁸ together with the carbon atom to which they are bonded    form the —X¹—(CH₂)_(r)—X²—, —(CH₂)_(s)—X³—, —(CH₂)_(t)—X³—CH₂—,    —(CH₂)_(v)—X³—(CH₂CH₂— or —(CH₂)_(w)— unit in which each of the    (CH₂) groups is substituted by m radicals from the group consisting    of halogen, methyl and (C₁-C₃)-alkoxy,    or-   R⁷ and R⁸ together with the carbon atom to which they are bonded    form the—O—N((C₁-C₃)-alkyl)-CHR¹⁰—CH₂— or —O—N═CR¹⁰—CH₂— unit in    which each of the (CH₂) groups is substituted by m radicals from the    group consisting of halogen and methyl;-   R⁹ is hydrogen, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₂-C₃)-alkenyl,    (C₂-C₄)-alkynyl, (C₃-C₅)-cycloalkyl,    (C₃-C₅)-cycloalkyl-(C₁-C₃)-alkyl, heteroaryl, heterocyclyl or    phenyl, where the three latter radicals are each substituted by s    radicals from the group consisting of halogen, nitro, cyano,    (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₆)-cycloalkyl,    (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl, (C₁-C₃)-alkylsulfonyl,    (C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy and    (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl;-   R¹⁰ is hydrogen or (C₁-C₃)-alkyl;-   X and Y are each independently O, SO₂, C═O, C═S, CR⁷R⁸, C═NOR¹⁰;-   X¹ and X² are each independently O, S, N(CH₃);-   X³ is O or S;-   m is 0, 1 or 2;-   n is 1 or 2;-   r is 2 or 3;-   s is 2, 3 or 4;-   t is 1, 2 or 3;-   u is 0, 1 or 2;-   v is 2 or 3;-   w is 2, 3, 4 or 5.

In all the formulae specified hereinafter, the substituents and symbolshave the same definition as in formula (I), unless defined differently.

Inventive compounds in which Q is Q1 or Q2 can be prepared, for example,by the method shown in scheme 1, by base-catalyzed reaction of abicyclic benzoyl chloride (II) with a 5-amino-1H-1,2,4-triazole or5-amino-1H-tetrazole (III):

B therein is CH or N. The bicyclic benzoyl chlorides of the formula (II)or their parent bicyclic benzoic acids are known in principle and can beprepared, for example, by the methods known in WO 96/25413, WO 97/09324,WO 97/30993, WO 97/08164, WO 98/49159, WO 98/35954, WO 98/12192, WO0014087 and EP 0636622.

Inventive compounds in which Q is Q1 or Q2 can also be prepared by themethod shown in scheme 2, by reaction of a benzoic acid of the formula(IV) with a 5-amino-1H-1,2,4-triazole or 5-amino-1H-tetrazole (III):

For the activation, it is possible to use dehydrating reagents which aretypically used for amidation reactions, for example1,1′-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC),2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P)etc.

Inventive compounds in which Q is Q1 or Q2 can also be prepared by themethod shown in scheme 3, by reaction of anN-(1H-1,2,4-triazol-5-yl)benzamide, N-(1H-tetrazol-5-yl)benzamide,N-(1H-1,2,4-triazol-5-yl)nicotinamide orN-(1H-tetrazol-5-yl)nicotinamide:

For this reaction shown in scheme 3, it is possible, for example, to usealkylating agents, for example alkyl halides or sulfonates or dialkylsulfates, in the presence of a base.

It may be appropriate to alter the sequence of reaction steps. Forinstance, benzoic acids bearing a sulfoxide cannot be converted directlyto their acid chlorides. One option here is first to prepare the amideto the thioether stage and then to oxidize the thioether to thesulfoxide.

The 5-amino-1H-tetrazoles of the formula (III) are either commerciallyavailable or can be prepared analogously to methods known from theliterature. For example, substituted 5-aminotetrazoles can be preparedfrom aminotetrazole by the method described in Journal of the AmericanChemical Society (1954), 76, 923-924:

In the above reaction, X is a leaving group such as iodine. Substituted5-aminotetrazoles can also be synthesized, for example, as described inJournal of the American Chemical Society (1954) 76, 88-89:

The 5-amino-1H-triazoles of the formula (III) are either commerciallyavailable or can be prepared analogously to methods known from theliterature. For example, substituted 5-aminotriazoles can be preparedfrom aminotriazole by the method described in Zeitschrift füer Chemie(1990), 30(12), 436-437:

Substituted 5-aminotriazoles can also be synthesized, for example, asdescribed in Chemische Berichte (1964), 97(2), 396-404:

Substituted 5-aminotriazoles can also be synthesized, for example, asdescribed in Angewandte Chemie (1963), 75, 918:

Inventive compounds in which Q is Q3 can be prepared, for example, bythe method shown in scheme 4, by base-catalyzed reaction of a bicyclicbenzoyl chloride (II) with a 4-amino-1,2,5-oxadiazole (VI):

Inventive compounds can also be prepared by the method described inscheme 5, by reacting a bicyclic benzoic acid of the formula (IV) with a4-amino-1,2,5-oxadiazole (VI):

For the activation, it is possible to use dehydrating reagents which aretypically used for amidation reactions, for example1,1′-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC),2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P)etc.

The 4-amino-1,2,5-oxadiazoles of the formula (VI) are eithercommercially available or known, or can be prepared analogously tomethods known from the literature. For example,3-alkyl-4-amino-1,2,5-oxadiazoles can be prepared from β-keto esters bythe method described in Russian Chemical Bulletin, Int. Ed., vol. 54, 4,p. 1032-1037 (2005):

3-Aryl-4-amino-1,2,5-oxadiazoles can be synthesized, for example, asdescribed in Russian Chemical Bulletin, 54(4), 1057-1059, (2005) orIndian Journal of Chemistry, Section B: Organic Chemistry IncludingMedicinal Chemistry, 26B(7), 690-2, (1987):

3-Amino-4-halo-1,2,5-oxadiazoles can be prepared, for example, by aSandmeyer reaction from the commercially available3,4-diamino-1,2,5-oxadiazole by the method described in HeteroatomChemistry 15(3), 199-207 (2004):

Nucleophilic R² radicals can be introduced into3-amino-1,2,5-oxadiazoles by Substitution of the leaving group L asdescribed in Journal of Chemical Research,Synopses, (6), 190, 1985 or inIzvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, (9), 2086-8, 1986 orin Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk,Seriya Khimicheskaya), 53(3), 596-614, 2004:

Collections of compounds of the formula (I) and/or salts thereof whichcan be synthesized by the abovementioned reactions can also be preparedin a parallelized manner, in which case this may be accomplished in amanual, partly automated or fully automated manner. It is possible, forexample, to automate the conduct of the reaction, the workup or thepurification of the products and/or intermediates. Overall, this isunderstood to mean a procedure as described, for example, by D. Tiebesin Combinatorial Chemistry—Synthesis, Analysis, Screening (editor:Günther Jung), Wiley, 1999, on pages 1 to 34.

For the parallelized conduct of the reaction and workup, it is possibleto use a number of commercially available instruments, for exampleCalypso reaction blocks from Barnstead International, Dubuque, Iowa52004-0797, USA or reaction stations from Radleys, Shirehill, SaffronWalden, Essex, CB11 3AZ, England, or MultiPROBE Automated Workstationsfrom Perkin Elmer, Waltham, Mass. 02451, USA. For the parallelizedpurification of compounds of the general formula (I) and salts thereofor of intermediates which occur in the course of preparation, availableapparatuses include chromatography apparatuses, for example from ISCO,Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses detailed lead to a modular procedure in which theindividual working steps are automated, but manual operations have to becarried out between the working steps. This can be circumvented by usingpartly or fully integrated automation systems in which the respectiveautomation modules are operated, for example, by robots. Automationsystems of this type can be purchased, for example, from Caliper,Hopkinton, Mass. 01748, USA.

The implementation of single or multiple synthesis steps can besupported by the use of polymer-supported reagents/scavenger resins. Thetechnical literature describes a number of experimental protocols, forexample ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Aside from the methods described here, the compounds of the generalformula (I) and salts thereof can be prepared completely or partially bysolid-phase supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bound to a synthesis resin.Solid-phase supported synthesis methods are described adequately in thetechnical literature, for example Barry A. Bunin in “The CombinatorialIndex”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis,Analysis, Screening (editor: Günther Jung), Wiley, 1999. The use ofsolid-phase-supported synthesis methods permits a number of protocolsknown from the literature, and these may again be executed manually orin an automated manner. The reactions can be performed, for example, bymeans of IRORI technology in microreactors from Nexus Biosystems, 12140Community Road, Poway, Calif. 92064, USA.

Either on a solid phase or in the liquid phase, the performance ofsingle or multiple synthesis steps can be supported by the use ofmicrowave technology. The technical literature describes a number ofexperimental protocols, for example Microwaves in Organic and MedicinalChemistry (editors: C. O. Kappe and A. Stadler), Wiley, 2005.

The preparation by the process described here gives compounds of theformula (I) and salts thereof in the form of substance collections,which are called libraries. The present invention also provideslibraries comprising at least two compounds of the formula (I) and saltsthereof.

The inventive compounds of the formula (I) (and/or salts thereof),collectively referred to hereinafter as “inventive compounds”, haveexcellent herbicidal efficacy against a broad spectrum of economicallyimportant monocotyledonous and dicotyledonous annual harmful plants. Theactive ingredients also have good control over perennial weed plantswhich are difficult to control and produce shoots from rhizomes, rootstocks or other perennial organs.

The present invention therefore also provides a method for controllingunwanted plants or for regulating the growth of plants, preferably inplant crops, in which one or more inventive compound(s) is/are appliedto the plants (for example weed plants such as monocotyledonous ordicotyledonous weeds or unwanted crop plants), to the seeds (for examplegrains, seeds or vegetative propagules such as tubers or shoot partswith buds) or to the area on which the plants grow (for example the areaunder cultivation). The inventive compounds can be deployed, forexample, prior to sowing (if appropriate also by incorporation into thesoil), prior to emergence or after emergence. Specific examples of somerepresentatives of the monocotyledonous and dicotyledonous weed florawhich can be controlled by the inventive compounds are as follows,though the enumeration is not intended to impose a restriction toparticular species:

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

If the inventive compounds are applied to the soil surface beforegermination, either the weed seedlings are prevented completely fromemerging or the weeds grow until they have reached the cotyledon stage,but then stop growing and, eventually, after three to four weeks havepassed, die completely.

If the active ingredients are applied post-emergence to the green partsof the plants, there is likewise stoppage of growth after the treatment,and the harmful plants remain at the growth stage of the time ofapplication, or they die completely after a certain time, such thatcompetition by the weeds, which is harmful to the crop plants, is thuseliminated very early and in a lasting manner.

Although the inventive compounds have excellent herbicidal activityagainst monocotyledonous and dicotyledonous weeds, crop plants ofeconomically important crops, for example dicotyledonous crops of thegenera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus,Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana,Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of thegenera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum,Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, especially Zea andTriticum, are damaged only to an insignificant extent, if at all,depending on the structure of the respective inventive compound and theapplication rate thereof. For these reasons, the present compounds arevery suitable for selective control of unwanted plant growth in plantcrops such as agriculturally useful plants or ornamentals.

In addition, the inventive compounds (depending on their particularstructure and the application rate deployed) have outstandinggrowth-regulating properties in crop plants. They intervene in theplant's own metabolism with a regulatory effect, and can thus be used tocontrol plant constituents and to facilitate harvesting, for example bytriggering desiccation and stunted growth. In addition, they are alsosuitable for general control and inhibition of unwanted vegetativegrowth without killing the plants. Inhibiting vegetative growth plays amajor role for many monocotyledonous and dicotyledonous crops, since,for example, this can reduce or completely prevent lodging.

By virtue of their herbicidal and plant growth-regulating properties,the active ingredients can also be used for control of harmful plants incrops of genetically modified plants or plants modified by conventionalmutagenesis. In general, the transgenic plants are notable for specialadvantageous properties, for example for resistances to certainpesticides, in particular certain herbicides, resistances to plantdiseases or organisms that cause plant diseases, such as certain insectsor microorganisms such as fungi, bacteria or viruses. Other particularproperties relate, for example, to the harvested material with regard toquantity, quality, storability, composition and specific constituents.For instance, there are known transgenic plants with an elevated starchcontent or altered starch quality, or with a different fatty acidcomposition in the harvested material.

With regard to transgenic crops, preference is given to the use of theinventive compounds in economically important transgenic crops of usefulplants and ornamentals, for example of cereals such as wheat, barley,rye, oats, millet/sorghum, rice and corn, or else crops of sugar beet,cotton, soybean, oilseed rape, potato, tomato, peas and othervegetables. Preferably, the inventive compounds can be used asherbicides in crops of useful plants which are resistant, or have beenmade resistant by recombinant means, to the phytotoxic effects of theherbicides.

Preference is given to the use of the inventive compounds or saltsthereof in economically important transgenic crops of useful plants andornamentals, for example of cereals such as wheat, barley, rye, oats,millet/sorghum, rice, cassava and corn, or else crops of sugar beet,cotton, soybean, oilseed rape, potato, tomato, peas and othervegetables. Preferably, the inventive compounds can be used asherbicides in crops of useful plants which are resistant, or have beenmade resistant by recombinant means, to the phytotoxic effects of theherbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to existing plants consist, for example, intraditional breeding methods and the generation of mutants.Alternatively, novel plants with modified properties can be generatedwith the aid of recombinant methods (see, for example, EP-A-0221044,EP-A-0131624). For example, there have been many descriptions of:

-   -   recombinant modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (e.g. WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to particular        herbicides of the glufosinate type (cf., for example,        EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or        the sulfonylureas (EP-A-0257993, US-A-5013659),    -   transgenic crop plants, for example cotton, with the ability to        produce Bacillus thuringiensis toxins (Bt toxins) which make the        plants resistant to particular pests (EP-A-0142924,        EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        cause an increased disease resistance (EPA 309862, EPA0464461),    -   genetically modified plants with reduced photorespiration, which        have higher yields and higher stress tolerance (EPA 0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which are notable for higher yields or        better quality,    -   transgenic crop plants which are notable for a combination, for        example, of the abovementioned novel properties (“gene        stacking”).

Numerous molecular biology techniques which can be used to produce noveltransgenic plants with modified properties are known in principle; see,for example, I. Potrykus and G. Spangenberg (eds.), Gene Transfer toPlants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelbergor Christou, “Trends in Plant Science” 1 (1996) 423-431).

For such recombinant manipulations, nucleic acid molecules which allowmutagenesis or a sequence change by recombination of DNA sequences canbe introduced into plasmids. With the aid of standard methods, it itpossible, for example, to undertake base exchanges, remove parts ofsequences or add natural or synthetic sequences. For the connection ofthe DNA fragments to one another, it is possible to add adapters orlinkers to the fragments; see, for example, Sambrook et al., 1989,Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring HarborLaboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene andKlone”, VCH Weinheim, 2nd edition, 1996.

The production of plant cells with a reduced activity of a gene productcan be achieved, for example, by the expression of at least oneappropriate antisense RNA, or of a sense RNA for achievement of acosuppression effect, or the expression of at least one appropriatelyconstructed ribozyme which specifically cleaves transcripts of theabovementioned gene product. For this purpose, it is firstly possible touse DNA molecules which comprise the entire coding sequence of a geneproduct including any flanking sequences present, or else DNA moleculeswhich comprise only parts of the coding sequence, in which case theseparts must be long enough to bring about an antisense effect in thecells. It is also possible to use DNA sequences which have a high degreeof homology to the coding sequences of a gene product, but are notcompletely identical.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, in order to achieve localization in a particularcompartment, it is possible, for example, to join the coding region toDNA sequences which ensure localization in a particular compartment.Such sequences are known to those skilled in the art (see, for example,Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl.Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991),95-106). The nucleic acid molecules can also be expressed in theorganelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques togive whole plants. In principle, the transgenic plants may be plants ofany desired plant species, i.e. both monocotyledonous and dicotyledonousplants.

Thus, it is possible to obtain transgenic plants whose properties arealtered by overexpression, suppression or inhibition of homologous(=natural) genes or gene sequences, or expression of heterologous(=foreign) genes or gene sequences.

Preferably, the inventive compounds can be used in transgenic cropswhich are resistant to growth regulators, for example dicamba, or toherbicides which inhibit essential plant enzymes, for exampleacetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS)or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from thegroup of the sulfonylureas, the glyphosates, glufosinates orbenzoylisoxazoles and analogous active ingredients.

On employment of the inventive active ingredients in transgenic crops,not only do the effects toward weed plants observed in other cropsoccur, but often also effects which are specific to application in theparticular transgenic crop, for example an altered or specificallywidened spectrum of weeds which can be controlled, altered applicationrates which can be used for the application, preferably goodcombinability with the herbicides to which the transgenic crop isresistant, and influencing of growth and yield of the transgenic cropplants.

The invention therefore also provides for the use of the inventivecompounds as herbicides for control of harmful plants in transgenic cropplants.

The inventive compounds can be applied in the form of wettable powders,emulsifiable concentrates, sprayable solutions, dusting products orgranules in the customary formulations. The invention therefore alsoprovides herbicidal and plant growth-regulating compositions whichcomprise the inventive compounds.

The inventive compounds can be formulated in various ways, according tothe biological and/or physicochemical parameters required. Examples ofpossible formulations include: wettable powders (WP), water-solublepowders (SP), water-soluble concentrates, emulsifiable concentrates(EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions,sprayable solutions, suspension concentrates (SC), oil- or water-baseddispersions, oil-miscible solutions, capsule suspensions (CS), dustingproducts (DP), seed-dressing products, granules for broadcasting andsoil application, granules (GR) in the form of microgranules, sprayablegranules, coated granules and adsorption granules, water-dispersiblegranules (WG), water-soluble granules (SG), ULV formulations,microcapsules and waxes.

These individual types of formulation are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th edition1986, Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker,N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G.Goodwin Ltd. London.

The necessary formulation assistants, such as inert materials,surfactants, solvents and further additives are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J., H. v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J., Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxideadducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie”, Volume 7, C. Hanser Verlag Munich, 4th Ed.1986.

On the basis of these formulations, it is also possible to producecombinations with other pesticidally active substances, for exampleinsecticides, acaricides, herbicides, fungicides, and with safeners,fertilizers and/or growth regulators, for example in the form of afinished formulation or as a tankmix. Suitable safeners are, forexample, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which can be dispersed uniformly inwater and, in addition to the active ingredient, apart from a diluent orinert substance, also comprise surfactants of the ionic and/or nonionictype (wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonateor else sodium oleoylmethyltaurinate. To produce the wettable powders,the herbicidal active ingredients are ground finely, for example incustomary apparatus such as hammer mills, blower mills and air-jetmills, and simultaneously or subsequently mixed with the formulationassistants.

Emulsifiable concentrates are produced by dissolving the activeingredient in an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene, or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more ionic and/or nonionic surfactants (emulsifiers). The emulsifiersused may, for example, be: calcium alkylarylsulfonates such as calciumdodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acidpolyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycolethers, propylene oxide-ethylene oxide condensation products, alkylpolyethers, sorbitan esters, for example sorbitan fatty acid esters, orpolyoxyethylene sorbitan esters, for example polyoxyethylene sorbitanfatty acid esters.

Dusting products are obtained by grinding the active ingredient withfinely distributed solid substances, for example talc, natural clays,such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They can beproduced, for example, by wet grinding by means of commercial bead millswith optional addition of surfactants as already listed above, forexample, for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants as already listedabove, for example, for the other formulation types.

Granules can be produced either by spraying the active ingredient ontoadsorptive granulated inert material or by applying active ingredientconcentrates by means of adhesives, for example polyvinyl alcohol,sodium polyacrylate or mineral oils, to the surface of carriersubstances, such as sand, kaolinites or granulated inert material.Suitable active ingredients can also be granulated in the mannercustomary for the production of fertilizer granules—if desired as amixture with fertilizers.

Water-dispersible granules are produced generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan granules, fluidized bed granules, extrudergranules and spray granules, see, for example, processes in“Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E.Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.;“Perry's Chemical Engineer's Handbook”, 5th ed., McGraw-Hill, New York1973, p. 8-57.

For further details regarding the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations contain generally 0.1 to 99% by weight,especially 0.1 to 95% by weight, of inventive compounds.

In wettable powders, the active ingredient concentration is, forexample, about 10 to 90% by weight; the remainder to 100% by weightconsists of the customary formulation constituents. In emulsifiableconcentrates, the active ingredient concentration may be about 1 to 90%and preferably 5 to 80% by weight.

Formulations in the form of dusts comprise 1 to 30% by weight of activeingredient, preferably usually 5 to 20% by weight of active ingredient;sprayable solutions contain about 0.05 to 80% and preferably 2 to 50% byweight of active ingredient. In the case of water-dispersible granules,the active ingredient content depends partly on whether the activecompound is present in liquid or solid form and on which granulationassistants, fillers, etc., are used. In the water-dispersible granules,the content of active ingredient is, for example, between 1 and 95% byweight, preferably between 10 and 80% by weight.

In addition, the active ingredient formulations mentioned optionallycomprise the respective customary tackifiers, wetting agents,dispersants, emulsifiers, penetrants, preservatives, antifreeze agentsand solvents, fillers, carriers and dyes, defoamers, evaporationinhibitors and agents which influence the pH and the viscosity.

On the basis of these formulations, it is also possible to producecombinations with other pesticidally active substances, for exampleinsecticides, acaricides, herbicides, fungicides, and with safeners,fertilizers and/or growth regulators, for example in the form of afinished formulation or as a tankmix.

Usable combination partners for the inventive compounds in mixtureformulations or in a tankmix are, for example, known active ingredientsbased on inhibition of, for example, acetolactate synthase, acetyl-CoAcarboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphatesynthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase,phytoendesaturase, photosystem I, photosystem II, protoporphyrinogenoxidase, as described, for example, in Weed Research 26 (1986) 441-445or “The Pesticide Manual”, 15th edition, The British Crop ProtectionCouncil and the Royal Soc. of Chemistry, 2009 and literature citedtherein. Examples of known herbicides or plant growth regulators whichcan be combined with the inventive compounds include the activeingredients which follow (the compounds are designated by the “commonname” according to the International Organization for Standardization(ISO) or by the chemical name or by the code number) and alwaysencompass all use forms, such as acids, salts, esters and isomers, suchas stereoisomers and optical isomers. In this list, one or else, in somecases, more than one application form is mentioned by way of example:

-   acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen,    acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim,    alloxydim-sodium, ametryne, amicarbazone, amidochlor, amidosulfuron,    aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate,    ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron,    aziprotryne, beflubutamid, benazolin, benazolin-ethyl, bencarbazone,    benfluralin, benfuresate, bensulide, bensulfuron,    bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon,    benzofenap, benzofluor, benzoylprop, bicyclopyrone, bifenox,    bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium,    bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron,    buminafos, busoxinone, butachlor, butafenacil, butamifos,    butenachlor, butralin, butroxydim, butylate, cafenstrole,    carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen,    chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron,    chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop,    chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron,    chlorimuron-ethyl, chlormequat-chloride, chlornitrofen,    chlorophthalim, chlorthal-dimethyl, chlortoluron, chlorsulfuron,    cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim,    clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop,    cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron,    cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron,    cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat,    cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon,    daminozide, dazomet, n-decanol, desmedipham, desmetryn,    detosyl-pyrazolate (DTP), diallate, dicamba, dichlobenil,    dichlorprop, dichlorprop-P, diclofop, diclofop-methyl,    diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl,    difenoxuron, difenzoquat, diflufenican, diflufenzopyr,    diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimepiperate,    dimethachlor, dimethametryn, dimethenamid, dimethenamid-P,    dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb,    diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr,    diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb,    ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethephon,    ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl,    ethoxysulfuron, etobenzanid, F-5331, i.e.    N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide,    F-7967, i.e.    3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione,    fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl,    fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop,    flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,    fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl,    fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron,    fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl,    flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl,    flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen,    fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate,    flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol,    flurenol-butyl, fluridone, flurochloridone, fluroxypyr,    fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet,    fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron,    forchlorfenuron, fosamine, furyloxyfen, gibberellic acid,    glufosinate, glufosinate-ammonium, glufosinate-P,    glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate,    glyphosate-isopropylammonium, H-9201, i.e.    O-(2,4-dimethyl-6-nitrophenyl) O-ethyl    isopropylphosphoramidothioate, halosafen, halosulfuron,    halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl,    haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl,    hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl    (2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl,    imazamox, imazamox-ammonium, imazapic, imazapyr,    imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium,    imazethapyr, imazethapyr-ammonium, imazosulfuron, inabenfide,    indanofan, indaziflam, indoleacetic acid (IAA), 4-indol-3-ylbutyric    acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, ioxynil,    ipfencarbazone, isocarbamid, isopropalin, isoproturon, isouron,    isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, i.e.    3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole,    karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic    hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop,    mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl,    mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl,    mecoprop-P-potassium, mefenacet, mefluidide, mepiquat-chloride,    mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron,    metam, metamifop, metamitron, metazachlor, metazasulfuron,    methazole, methiopyrsulfuron, methiozolin, methoxyphenone,    methyldymron, 1-methylcyclopropene, methyl isothiocyanate,    metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam,    metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate,    monalide, monocarbamide, monocarbamide dihydrogensulfate,    monolinuron, monosulfuron, monosulfuron ester, monuron, MT-128, i.e.    6-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-5-methyl-N-phenylpyridazine-3-amine,    MT-5950, i.e.    N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011,    naproanilide, napropamide, naptalam, NC-310, i.e.    4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon,    nicosulfuron, nipyraclofen, nitralin, nitrofen,    nitrophenolate-sodium (isomer mixture), nitrofluorfen, nonanoic    acid, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl,    oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazole,    paraquat, paraquat dichloride, pelargonic acid (nonanoic acid),    pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone,    perfluidone, pethoxamid, phenisopham, phenmedipham,    phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos,    pirifenop, pirifenop-butyl, pretilachlor, primisulfuron,    primisulfuron-methyl, probenazole, profluazole, procyazine,    prodiamine, prifluraline, profoxydim, prohexadione,    prohexadione-calcium, prohydrojasmone, prometon, prometryn,    propachlor, propanil, propaquizafop, propazine, propham,    propisochlor, propoxycarbazone, propoxycarbazone-sodium,    propyrisulfuron, propyzamide, prosulfalin, prosulfocarb,    prosulfuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl,    pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron,    pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz,    pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim,    pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac,    pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium,    pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine,    quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl,    quizalofop-P-tefuryl, rimsulfuron, saflufenacil, secbumeton,    sethoxydim, siduron, simazine, simetryn, SN-106279, i.e. methyl    (2R)-2-({7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl}oxy)propanoate,    sulcotrione, sulfallate (CDEC), sulfentrazone, sulfometuron,    sulfometuron-methyl, sulfosate (glyphosate-trimesium),    sulfosulfuron, SYN-523, SYP-249, i.e.    1-ethoxy-3-methyl-1-oxobut-3-en-2-yl    5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300,    i.e.    1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione,    tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione,    tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,    terbuthylazine, terbutryne, thenylchlor, thiafluamide, thiazafluron,    thiazopyr, thidiazimin, thidiazuron, thiencarbazone,    thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl,    thiobencarb, tiocarbazil, topramezone, tralkoxydim, triafamone,    triallate, triasulfuron, triaziflam, triazofenamide, tribenuron,    tribenuron-methyl, trichloroacetic acid (TCA), triclopyr,    tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium,    trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon,    trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole,    uniconazole-P, vernolate, ZJ-0862, i.e.    3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline,    and the following compounds:

For application, the formulations in commercial form are, ifappropriate, diluted in a customary manner, for example in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules with water. Dust-type formulations, granulesfor soil application or granules for broadcasting and sprayablesolutions are not normally diluted further with other inert substancesprior to application.

The required application rate of the compounds of the formula (I) varieswith the external conditions, including temperature, humidity and thetype of herbicide used. It can vary within wide limits, for examplebetween 0.001 and 1.0 kg/ha or more active substance, but it ispreferably between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. CHEMICAL EXAMPLES 1. Synthesis of4-chloro-3-methoxy-N-(4-methyl-1,2,5-oxadiazol-3-yl)-2,3-dihydro-1-benzothiophene-5-carboxamide1,1-dioxide (table example No. 1928)

1.00 g (3.14 mmol) of4-chloro-3-methoxy-2,3-dihydro-1-benzothiophene-5-carboxylic acid1,1-dioxide and 0.33 g (3.15 mmol) of4-methyl-1,2,5-oxadiazol-3-yl-amine were dissolved at room temperature(RT) in 35 ml of CH₂Cl₂, 3.02 g (4.74 mmol) of2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50%solution in THF) were added and the mixture was stirred at RT for 1 h.Subsequently, 2.18 ml (15.64 mmol) of triethylamine and 75 mg (0.61mmol) of 4-dimethylaminopyridine (DMAP) were added and the whole mixturewas stirred at RT for 16 h. This was followed by washing with water andtwice with 6N hydrochloric acid, drying of the organic phase over Na₂SO₄and filtration with suction through silica gel, washing through with 1:2heptane/ethyl acetate and concentration. Yield 708 mg (63%).

¹H NMR (CDCl₃): δ=2.44 (s,3H), 3.53 (s,3H), 3.57 (dd,1H), 3.71 (d,1H),5.15 (d,1H), 7.55 (d,1H), 7.74 (d,1H), 9.40 (s,1H)

2. Synthesis of4-chloro-N-(1-methyl-1H-1,2,4-triazol-5-yl)-2,3-dihydro-1-benzothiophen-5-carboxamide1,1-dioxide (table example No. 1545)

0.80 g (3.24 mmol) of 4-chloro-2,3-dihydro-1-benzothiophene-5-carboxylicacid 1,1-dioxide, 0.72 g (2.43 mmol) ofdi(1-methyl-1H-1,2,4-triazol-5-amine) sulfate and 20 mg (0.164 mmol) ofDMAP were initially charged in 5 ml of pyridine, 0.65 g (5.35 mmol) ofthionyl chloride were added and the mixture was stirred at 70° C. for 1h. Subsequently, 0.5 ml of water was added, and the mixture was stirredfor a further 30 min, acidified with saturated KHSO₄ solution andextracted three times with 100 ml each time of ethyl acetate. Thecombined organic phases were washed with saturated NaHCO₃ solution,dried over Na₂SO₄ and concentrated. The residue was purified by columnchromatography (silica gel, heptane/ethyl acetate). Yield 642 mg (61%).

¹H NMR (DMSO-d₆): δ=3.40 (t,2H), 3.74 (t,2H), 3.79 (s,3H), 7.89 (br,3H),11.39 (s,1H)

3. Synthesis ofN-(1-ethyl-1H-tetrazol-5-yl)-4,4,5,8-tetramethyl-3,4-dihydro-2H-thiochromene-6-carboxamide1,1-dioxide (table example No. 189)

1.00 g (3.54 mmol) of4,4,5,8-tetramethyl-3,4-dihydro-2H-thiochromene-6-carboxylic acid1,1-dioxide, 0.63 g (5.32 mmol) of 1-ethyl-5-aminotetrazole and 23 mg(0.188 mmol) of DMAP were initially charged in 7 ml of pyridine, 0.71 g(5.86 mmol) of thionyl chloride were added and the mixture was stirredat 70° C. for 1 h.

Subsequently, 0.5 ml of water was added, and the mixture was stirred fora further 30 min, acidified with saturated KHSO₄ solution and extractedthree times with 100 ml each time of ethyl acetate. The combined organicphases were washed with saturated NaHCO₃ solution, dried over Na₂SO₄ andconcentrated. The residue was purified by column chromatography (silicagel, heptane/ethyl acetate). Yield 492 mg (37%).

¹H NMR (CDCl₃): δ=1.56 (s,6H), 1.64 (t,3H), 2.36 (dd,2H), 2.65 (s,3H),2.77 (s,3H), 3.43 (dd,2H), 4.46 (q,2H), 7.37 (s,3H), 10.16 (s,1H)

The examples listed in the tables below were prepared analogously to theabovementioned methods or are obtainable analogously to theabovementioned methods. The compounds listed in the tables below arevery particularly preferred.

The abbreviations used mean:

Et = ethyl Me = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr =cyclopropyl Ph = phenyl

TABLE 1 Inventive compounds of the general formula (I) in which Q is Q1,Y is S(O)_(m), R⁵ is hydrogen and n is 2

No. R¹ R³ R⁴ m X 1H NMR  1. Me Me Me 0 CH₂  2. Me Me Me 1 CH₂  3. Me MeMe 2 CH₂  4. Me Me Me 0 CHMe  5. Me Me Me 1 CHMe  6. Me Me Me 2 CHMe  7.Me Me Me 0 C(CH₃)₂ CDCl3, 400 MHz: 1.49 (s, 6H), 2.04 (dd, 2H), 2.28 (s,3H), 2.62 (s, 3H), 2.98 (dd, 2H), 4.10 (s, 3H), 7.22 (s, 1H), 8.81 (s,1H)  8. Me Me Me 1 C(CH₃)₂  9. Me Me Me 2 C(CH₃)₂ CDCl3, 400 MHz: 1.55(s, 6H), 2.38 (dd, 2H), 2.64 (s, 3H), 2.81 (s, 3H), 3.43 (dd, 2H), 4.10(s, 3H), 7.33 (s, 1H), 8.87 (s, 1H)  10. Me Me Me 0 C(OC₂H₄O)  11. Me MeMe 1 C(OC₂H₄O)  12. Me Me Me 2 C(OC₂H₄O)  13. Me Me Me 0 C(SC₂H₄S)  14.Me Me Me 1 C(SC₂H₄S)  15. Me Me Me 2 C(SC₂H₄S)  16. Me Me Me 0 CHOMe 17. Me Me Me 1 CHOMe  18. Me Me Me 2 CHOMe  19. Me Me Me 0 CHOEt  20.Me Me Me 1 CHOEt  21. Me Me Me 2 CHOEt  22. Me Me Me 0 CHOiPr  23. Me MeMe 1 CHOiPr  24. Me Me Me 2 CHOiPr  25. Me Me Me 0 CHOCH₂cPr  26. Me MeMe 1 CHOCH₂cPr  27. Me Me Me 2 CHOCH₂cPr  28. Me Me Me 0 CHOC₂H₄OMe  29.Me Me Me 1 CHOC₂H₄OMe  30. Me Me Me 2 CHOC₂H₄OMe  31. Me Me Me 0CHOCH₂CCH  32. Me Me Me 1 CHOCH₂CCH  33. Me Me Me 2 CHOCH₂CCH  34. Me MeMe 0 CHOCH₂CH═CH₂  35. Me Me Me 1 CHOCH₂CH═CH₂  36. Me Me Me 2CHOCH₂CH═CH₂  37. Me Me Me 0

 38. Me Me Me 1

 39. Me Me Me 2

 40. Me Me Me 0

CDCl3, 400 MHz: 8.28-8.25 (m, 2H), 8.19 (m, 1H), 7.62 (s, 1H), 6.52 (m,1H), 4.13 (s, 3H), 3.81 (m, 1H), 3.30 (m, 1H), 2.92-2.74 (m, 2H), 2.80(s, 3H), 2.32 (s, 3H)  41. Me Me Me 1

 42. Me Me Me 2

 43. Me Me Me 0

 44. Me Me Me 1

 45. Me Me Me 2

 46. Me Me Me 0

 47. Me Me Me 1

 48. Me Me Me 2

 49. Me Me Me 0

 50. Me Me Me 1

 51. Me Me Me 2

 52. Me Me Me 0 CHOC₂H₄F  53. Me Me Me 1 CHOC₂H₄F  54. Me Me Me 2CHOC₂H₄F  55. Me Me Me 0 C═NOMe  56. Me Me Me 1 C═NOMe  57. Me Me Me 2C═NOMe  58. Me Me Me 0 C═NOCH₂CCH  59. Me Me Me 1 C═NOCH₂CCH  60. Me MeMe 2 C═NOCH₂CCH  61. Me Me Me 0 C═NOCH₂CH═CH₂  62. Me Me Me 1C═NOCH₂CH═CH₂  63. Me Me Me 2 C═NOCH₂CH═CH₂  64. Me Me Me 0 C═O  65. MeMe Me 1 C═O  66. Me Me Me 2 C═O  67. Me Me Me 0 C═S  68. Me Me Me 1 C═S 69. Me Me Me 2 C═S  70. Me Me Me 0 C═S  71. Me Me Me 1 C═S  72. Me MeMe 2 C═S  73. Me Me Me 0 C═N—N(CH₃)₂  74. Me Me Me 1 C═N—N(CH₃)₂  75. MeMe Me 2 C═N—N(CH₃)₂  76. Me Me Me 0 O  77. Me Me Me 1 O  78. Me Me Me 2O  79. Me Me Me 0 S  80. Me Me Me 1 S  81. Me Me Me 2 S  82. Me Me Me 0SO  83. Me Me Me 1 SO  84. Me Me Me 2 SO  85. Me Me Me 0 SO₂  86. Me MeMe 1 SO₂  87. Me Me Me 2 SO₂  88. Me Me Me 0 NMe  89. Me Me Me 1 NMe 90. Me Me Me 2 NMe  91. Me Me H 0 CH₂  92. Me Me H 1 CH₂  93. Me Me H 2CH₂  94. Me Me H 0 CHMe  95. Me Me H 1 CHMe  96. Me Me H 2 CHMe  97. MeMe H 0 C(CH₃)₂  98. Me Me H 1 C(CH₃)₂  99. Me Me H 2 C(CH₃)₂ 100. Me MeH 0 C(OC₂H₄O) 101. Me Me H 1 C(OC₂H₄O) 102. Me Me H 2 C(OC₂H₄O) 103. MeMe H 0 C(SC₂H₄S) 104. Me Me H 1 C(SC₂H₄S) 105. Me Me H 2 C(SC₂H₄S) 106.Me Me H 0 CHOMe 107. Me Me H 1 CHOMe 108. Me Me H 2 CHOMe 109. Me Me H 0CHOEt 110. Me Me H 1 CHOEt 111. Me Me H 2 CHOEt 112. Me Me H 0 CHOiPr113. Me Me H 1 CHOiPr 114. Me Me H 2 CHOiPr 115. Me Me H 0 CHOCH₂cPr116. Me Me H 1 CHOCH₂cPr 117. Me Me H 2 CHOCH₂cPr 118. Me Me H 0CHOC₂H₄OMe 119. Me Me H 1 CHOC₂H₄OMe 120. Me Me H 2 CHOC₂H₄OMe 121. MeMe H 0 CHOCH₂CCH 122. Me Me H 1 CHOCH₂CCH 123. Me Me H 2 CHOCH₂CCH 124.Me Me H 0 CHOCH₂CH═CH₂ 125. Me Me H 1 CHOCH₂CH═CH₂ 126. Me Me H 2CHOCH₂CH═CH₂ 127. Me Me H 0

128. Me Me H 1

129. Me Me H 2

130. Me Me H 0

131. Me Me H 1

132. Me Me H 2

133. Me Me H 0

134. Me Me H 1

135. Me Me H 2

136. Me Me H 0

137. Me Me H 1

138. Me Me H 2

139. Me Me H 0

140. Me Me H 1

141. Me Me H 2

142. Me Me H 0 CHOC₂H₄F 143. Me Me H 1 CHOC₂H₄F 144. Me Me H 2 CHOC₂H₄F145. Me Me H 0 C═NOMe 146. Me Me H 1 C═NOMe 147. Me Me H 2 C═NOMe 148.Me Me H 0 C═NOCH₂CCH 149. Me Me H 1 C═NOCH₂CCH 150. Me Me H 2 C═NOCH₂CCH151. Me Me H 0 C═NOCH₂CH═CH₂ 152. Me Me H 1 C═NOCH₂CH═CH₂ 153. Me Me H 2C═NOCH₂CH═CH₂ 154. Me Me H 0 C═O 155. Me Me H 1 C═O 156. Me Me H 2 C═O157. Me Me H 0 C═S 158. Me Me H 1 C═S 159. Me Me H 2 C═S 160. Me Me H 0C═S 161. Me Me H 1 C═S 162. Me Me H 2 C═S 163. Me Me H 0 C═N—N(CH₃)₂164. Me Me H 1 C═N—N(CH₃)₂ 165. Me Me H 2 C═N—N(CH₃)₂ 166. Me Me H 0 O167. Me Me H 1 O 168. Me Me H 2 O 169. Me Me H 0 S 170. Me Me H 1 S 171.Me Me H 2 S 172. Me Me H 0 SO 173. Me Me H 1 SO 174. Me Me H 2 SO 175.Me Me H 0 SO₂ 176. Me Me H 1 SO₂ 177. Me Me H 2 SO₂ 178. Me Me H 0 NMe179. Me Me H 1 NMe 180. Me Me H 2 NMe 181. Et Me Me 0 CH₂ 182. Et Me Me1 CH₂ 183. Et Me Me 2 CH₂ 184. Et Me Me 0 CHMe 185. Et Me Me 1 CHMe 186.Et Me Me 2 CHMe 187. Et Me Me 0 C(CH₃)₂ CDCl3, 400 MHz: 1.49 (s, 6H),1.61 (t, 3H), 2.04 (dd, 2H), 2.29 (s, 3H), 2.62 (s, 3H), 2.99 (dd, 2H),4.46 (q, 2H), 7.23 (s, 1H), 9.12 (s, 1H) 188. Et Me Me 1 C(CH₃)₂ 189. EtMe Me 2 C(CH₃)₂ CDCl3, 400 MHz: 1.56 (s, 6H), 1.64 (t, 3H), 2.36 (dd,2H), 2.65 (s, 3H), 2.77 (s, 3H), 3.43 (dd, 2H), 4.46 (q, 2H), 7.37 (s,1H), 10.16 (s, 1H) 190. Et Me Me 0 C(OC₂H₄O) 191. Et Me Me 1 C(OC₂H₄O)192. Et Me Me 2 C(OC₂H₄O) 193. Et Me Me 0 C(SC₂H₄S) 194. Et Me Me 1C(SC₂H₄S) 195. Et Me Me 2 C(SC₂H₄S) 196. Et Me Me 0 CHOMe 197. Et Me Me1 CHOMe 198. Et Me Me 2 CHOMe 199. Et Me Me 0 CHOEt 200. Et Me Me 1CHOEt 201. Et Me Me 2 CHOEt 202. Et Me Me 0 CHOiPr 203. Et Me Me 1CHOiPr 204. Et Me Me 2 CHOiPr 205. Et Me Me 0 CHOCH₂cPr 206. Et Me Me 1CHOCH₂cPr 207. Et Me Me 2 CHOCH₂cPr 208. Et Me Me 0 CHOC₂H₄OMe 209. EtMe Me 1 CHOC₂H₄OMe 210. Et Me Me 2 CHOC₂H₄OMe 211. Et Me Me 0 CHOCH₂CCH212. Et Me Me 1 CHOCH₂CCH 213. Et Me Me 2 CHOCH₂CCH 214. Et Me Me 0CHOCH₂CH═CH₂ 215. Et Me Me 1 CHOCH₂CH═CH₂ 216. Et Me Me 2 CHOCH₂CH═CH₂217. Et Me Me 0

218. Et Me Me 1

219. Et Me Me 2

220. Et Me Me 0

221. Et Me Me 1

222. Et Me Me 2

223. Et Me Me 0

224. Et Me Me 1

225. Et Me Me 2

226. Et Me Me 0

227. Et Me Me 1

228. Et Me Me 2

229. Et Me Me 0

230. Et Me Me 1

231. Et Me Me 2

232. Et Me Me 0 CHOC₂H₄F 233. Et Me Me 1 CHOC₂H₄F 234. Et Me Me 2CHOC₂H₄F 235. Et Me Me 0 C═NOMe 236. Et Me Me 1 C═NOMe 237. Et Me Me 2C═NOMe 238. Et Me Me 0 C═NOCH₂CCH 239. Et Me Me 1 C═NOCH₂CCH 240. Et MeMe 2 C═NOCH₂CCH 241. Et Me Me 0 C═NOCH₂CH═CH₂ 242. Et Me Me 1C═NOCH₂CH═CH₂ 243. Et Me Me 2 C═NOCH₂CH═CH₂ 244. Et Me Me 0 C═O 245. EtMe Me 1 C═O 246. Et Me Me 2 C═O 247. Et Me Me 0 C═S 248. Et Me Me 1 C═S249. Et Me Me 2 C═S 250. Et Me Me 0 C═S 251. Et Me Me 1 C═S 252. Et MeMe 2 C═S 253. Et Me Me 0 C═N—N(CH₃)₂ 254. Et Me Me 1 C═N—N(CH₃)₂ 255. EtMe Me 2 C═N—N(CH₃)₂ 256. Et Me Me 0 O 257. Et Me Me 1 O 258. Et Me Me 2O 259. Et Me Me 0 S 260. Et Me Me 1 S 261. Et Me Me 2 S 262. Et Me Me 0SO 263. Et Me Me 1 SO 264. Et Me Me 2 SO 265. Et Me Me 0 SO₂ 266. Et MeMe 1 SO₂ 267. Et Me Me 2 SO₂ 268. Et Me Me 0 NMe 269. Et Me Me 1 NMe270. Et Me Me 2 NMe 271. Et Me H 0 CH₂ 272. Et Me H 1 CH₂ 273. Et Me H 2CH₂ 274. Et Me H 0 CHMe 275. Et Me H 1 CHMe 276. Et Me H 2 CHMe 277. EtMe H 0 C(CH₃)₂ 278. Et Me H 1 C(CH₃)₂ 279. Et Me H 2 C(CH₃)₂ 280. Et MeH 0 C(OC₂H₄O) 281. Et Me H 1 C(OC₂H₄O) 282. Et Me H 2 C(OC₂H₄O) 283. EtMe H 0 C(SC₂H₄S) 284. Et Me H 1 C(SC₂H₄S) 285. Et Me H 2 C(SC₂H₄S) 286.Et Me H 0 CHOMe 287. Et Me H 1 CHOMe 288. Et Me H 2 CHOMe 289. Et Me H 0CHOEt 290. Et Me H 1 CHOEt 291. Et Me H 2 CHOEt 292. Et Me H 0 CHOiPr293. Et Me H 1 CHOiPr 294. Et Me H 2 CHOiPr 295. Et Me H 0 CHOCH₂cPr296. Et Me H 1 CHOCH₂cPr 297. Et Me H 2 CHOCH₂cPr 298. Et Me H 0CHOC₂H₄OMe 299. Et Me H 1 CHOC₂H₄OMe 300. Et Me H 2 CHOC₂H₄OMe 301. EtMe H 0 CHOCH₂CCH 302. Et Me H 1 CHOCH₂CCH 303. Et Me H 2 CHOCH₂CCH 304.Et Me H 0 CHOCH₂CH═CH₂ 305. Et Me H 1 CHOCH₂CH═CH₂ 306. Et Me H 2CHOCH₂CH═CH₂ 307. Et Me H 0

308. Et Me H 1

309. Et Me H 2

310. Et Me H 0

311. Et Me H 1

312. Et Me H 2

313. Et Me H 0

314. Et Me H 1

315. Et Me H 2

316. Et Me H 0

317. Et Me H 1

318. Et Me H 2

319. Et Me H 0

320. Et Me H 1

321 Et Me H 2

322. Et Me H 0 CHOC₂H₄F 323. Et Me H 1 CHOC₂H₄F 324. Et Me H 2 CHOC₂H₄F325. Et Me H 0 C═NOMe 326. Et Me H 1 C═NOMe 327. Et Me H 2 C═NOMe 328.Et Me H 0 C═NOCH₂CCH 329. Et Me H 1 C═NOCH₂CCH 330. Et Me H 2 C═NOCH₂CCH331. Et Me H 0 C═NOCH₂CH═CH₂ 332. Et Me H 1 C═NOCH₂CH═CH₂ 333. Et Me H 2C═NOCH₂CH═CH₂ 334. Et Me H 0 C═O 335. Et Me H 1 C═O 336. Et Me H 2 C═O337. Et Me H 0 C═S 338. Et Me H 1 C═S 339. Et Me H 2 C═S 340. Et Me H 0C═S 341. Et Me H 1 C═S 342. Et Me H 2 C═S 343. Et Me H 0 C═N—N(CH₃)₂344. Et Me H 1 C═N—N(CH₃)₂ 345. Et Me H 2 C═N—N(CH₃)₂ 346. Et Me H 0 O347. Et Me H 1 O 348. Et Me H 2 O 349. Et Me H 0 S 350. Et Me H 1 S 351.Et Me H 2 S 352. Et Me H 0 SO 353. Et Me H 1 SO 354. Et Me H 2 SO 355.Et Me H 0 SO₂ 356. Et Me H 1 SO₂ 357. Et Me H 2 SO₂ 358. Et Me H 0 NMe359. Et Me H 1 NMe 360. Et Me H 2 NMe

TABLE 2 Inventive compounds of the general formula (I) in which Q is Q2,Y is S(O)_(m), R⁵ is hydrogen and n is 2

Number R¹ R³ R⁴ m X 1H NMR 361. Me Me Me 0 CH₂ 362. Me Me Me 1 CH₂ 363.Me Me Me 2 CH₂ 364. Me Me Me 0 CHMe 365. Me Me Me 1 CHMe 366. Me Me Me 2CHMe 367. Me Me Me 0 C(CH₃)₂ 368. Me Me Me 1 C(CH₃)₂ 369. Me Me Me 2C(CH₃)₂ 370. Me Me Me 0 C(OC₂H₄O) 371. Me Me Me 1 C(OC₂H₄O) 372. Me MeMe 2 C(OC₂H₄O) 373. Me Me Me 0 C(SC₂H₄S) 374. Me Me Me 1 C(SC₂H₄S) 375.Me Me Me 2 C(SC₂H₄S) 376. Me Me Me 0 CHOMe 377. Me Me Me 1 CHOMe 378. MeMe Me 2 CHOMe 379. Me Me Me 0 CHOEt 380. Me Me Me 1 CHOEt 381. Me Me Me2 CHOEt 382. Me Me Me 0 CHOiPr 383. Me Me Me 1 CHOiPr 384. Me Me Me 2CHOiPr 385. Me Me Me 0 CHOCH₂cPr 386. Me Me Me 1 CHOCH₂cPr 387. Me Me Me2 CHOCH₂cPr 388. Me Me Me 0 CHOC₂H₄OMe 389. Me Me Me 1 CHOC₂H₄OMe 390.Me Me Me 2 CHOC₂H₄OMe 391. Me Me Me 0 CHOCH₂CCH 392. Me Me Me 1CHOCH₂CCH 393. Me Me Me 2 CHOCH₂CCH 394. Me Me Me 0 CHOCH₂CH═CH₂ 395. MeMe Me 1 CHOCH₂CH═CH₂ 396. Me Me Me 2 CHOCH₂CH═CH₂ 397. Me Me Me 0

398. Me Me Me 1

399. Me Me Me 2

400. Me Me Me 0

401. Me Me Me 1

402. Me Me Me 2

403. Me Me Me 0

404. Me Me Me 1

405. Me Me Me 2

406. Me Me Me 0

407. Me Me Me 1

408. Me Me Me 2

409. Me Me Me 0

410. Me Me Me 1

411. Me Me Me 2

412. Me Me Me 0 CHOC₂H₄F 413. Me Me Me 1 CHOC₂H₄F 414. Me Me Me 2CHOC₂H₄F 415. Me Me Me 0 C═NOMe 416. Me Me Me 1 C═NOMe 417. Me Me Me 2C═NOMe 418. Me Me Me 0 C═NOCH₂CCH 419. Me Me Me 1 C═NOCH₂CCH 420. Me MeMe 2 C═NOCH₂CCH 421. Me Me Me 0 C═NOCH₂CH═CH₂ 422. Me Me Me 1C═NOCH₂CH═CH₂ 423. Me Me Me 2 C═NOCH₂CH═CH₂ 424. Me Me Me 0 C═O 425. MeMe Me 1 C═O 426. Me Me Me 2 C═O 427. Me Me Me 0 C═S 428. Me Me Me 1 C═S429. Me Me Me 2 C═S 430. Me Me Me 0 C═S 431. Me Me Me 1 C═S 432. Me MeMe 2 C═S 433. Me Me Me 0 C═N—N(CH₃)₂ 434. Me Me Me 1 C═N—N(CH₃)₂ 435. MeMe Me 2 C═N—N(CH₃)₂ 436. Me Me Me 0 O 437. Me Me Me 1 O 438. Me Me Me 2O 439. Me Me Me 0 S 440. Me Me Me 1 S 441. Me Me Me 2 S 442. Me Me Me 0SO 443. Me Me Me 1 SO 444. Me Me Me 2 SO 445. Me Me Me 0 SO₂ 446. Me MeMe 1 SO₂ 447. Me Me Me 2 SO₂ 448. Me Me Me 0 NMe 449. Me Me Me 1 NMe450. Me Me Me 2 NMe 451. Me Me H 0 CH₂ 452. Me Me H 1 CH₂ 453. Me Me H 2CH₂ 454. Me Me H 0 CHMe 455. Me Me H 1 CHMe 456. Me Me H 2 CHMe 457. MeMe H 0 C(CH₃)₂ 458. Me Me H 1 C(CH₃)₂ 459. Me Me H 2 C(CH₃)₂ 460. Me MeH 0 C(OC₂H₄O) 461. Me Me H 1 C(OC₂H₄O) 462. Me Me H 2 C(OC₂H₄O) 463. MeMe H 0 C(SC₂H₄S) 464. Me Me H 1 C(SC₂H₄S) 465. Me Me H 2 C(SC₂H₄S) 466.Me Me H 0 CHOMe 467. Me Me H 1 CHOMe 468. Me Me H 2 CHOMe 469. Me Me H 0CHOEt 470. Me Me H 1 CHOEt 471. Me Me H 2 CHOEt 472. Me Me H 0 CHOiPr473. Me Me H 1 CHOiPr 474. Me Me H 2 CHOiPr 475. Me Me H 0 CHOCH₂cPr476. Me Me H 1 CHOCH₂cPr 477. Me Me H 2 CHOCH₂cPr 478. Me Me H 0CHOC₂H₄OMe 479. Me Me H 1 CHOC₂H₄OMe 480. Me Me H 2 CHOC₂H₄OMe 481. MeMe H 0 CHOCH₂CCH 482. Me Me H 1 CHOCH₂CCH 483. Me Me H 2 CHOCH₂CCH 484.Me Me H 0 CHOCH₂CH═CH₂ 485. Me Me H 1 CHOCH₂CH═CH₂ 486. Me Me H 2CHOCH₂CH═CH₂ 487. Me Me H 0

488. Me Me H 1

489. Me Me H 2

490. Me Me H 0

491. Me Me H 1

492. Me Me H 2

493. Me Me H 0

494. Me Me H 1

495. Me Me H 2

496. Me Me H 0

497. Me Me H 1

498. Me Me H 2

499. Me Me H 0

500. Me Me H 1

501. Me Me H 2

502. Me Me H 0 CHOC₂H₄F 503. Me Me H 1 CHOC₂H₄F 504. Me Me H 2 CHOC₂H₄F505. Me Me H 0 C═NOMe 506. Me Me H 1 C═NOMe 507. Me Me H 2 C═NOMe 508.Me Me H 0 C═NOCH₂CCH 509. Me Me H 1 C═NOCH₂CCH 510. Me Me H 2 C═NOCH₂CCH511. Me Me H 0 C═NOCH₂CH═CH₂ 512. Me Me H 1 C═NOCH₂CH═CH₂ 513. Me Me H 2C═NOCH₂CH═CH₂ 514. Me Me H 0 C═O 515. Me Me H 1 C═O 516. Me Me H 2 C═O517. Me Me H 0 C═S 518. Me Me H 1 C═S 519. Me Me H 2 C═S 520. Me Me H 0C═S 521. Me Me H 1 C═S 522. Me Me H 2 C═S 523. Me Me H 0 C═N—N(CH₃)₂524. Me Me H 1 C═N—N(CH₃)₂ 525. Me Me H 2 C═N—N(CH₃)₂ 526. Me Me H 0 O527. Me Me H 1 O 528. Me Me H 2 O 529. Me Me H 0 S 530. Me Me H 1 S 531.Me Me H 2 S 532. Me Me H 0 SO 533. Me Me H 1 SO 534. Me Me H 2 SO 535.Me Me H 0 SO₂ 536. Me Me H 1 SO₂ 537. Me Me H 2 SO₂ 538. Me Me H 0 NMe539. Me Me H 1 NMe 540. Me Me H 2 NMe 541. Et Me Me 0 CH₂ 542. Et Me Me1 CH₂ 543. Et Me Me 2 CH₂ 544. Et Me Me 0 CHMe 545. Et Me Me 1 CHMe 546.Et Me Me 2 CHMe 547. Et Me Me 0 C(CH₃)₂ 548. Et Me Me 1 C(CH₃)₂ 549. EtMe Me 2 C(CH₃)₂ 550. Et Me Me 0 C(OC₂H₄O) 551. Et Me Me 1 C(OC₂H₄O) 552.Et Me Me 2 C(OC₂H₄O) 553. Et Me Me 0 C(SC₂H₄S) 554. Et Me Me 1 C(SC₂H₄S)555. Et Me Me 2 C(SC₂H₄S) 556. Et Me Me 0 CHOMe 557. Et Me Me 1 CHOMe558. Et Me Me 2 CHOMe 559. Et Me Me 0 CHOEt 560. Et Me Me 1 CHOEt 561.Et Me Me 2 CHOEt 562. Et Me Me 0 CHOiPr 563. Et Me Me 1 CHOiPr 564. EtMe Me 2 CHOiPr 565. Et Me Me 0 CHOCH₂cPr 566. Et Me Me 1 CHOCH₂cPr 567.Et Me Me 2 CHOCH₂cPr 568. Et Me Me 0 CHOC₂H₄OMe 569. Et Me Me 1CHOC₂H₄OMe 570. Et Me Me 2 CHOC₂H₄OMe 571. Et Me Me 0 CHOCH₂CCH 572. EtMe Me 1 CHOCH₂CCH 573. Et Me Me 2 CHOCH₂CCH 574. Et Me Me 0 CHOCH₂CH═CH₂575. Et Me Me 1 CHOCH₂CH═CH₂ 576. Et Me Me 2 CHOCH₂CH═CH₂ 577. Et Me Me0

578. Et Me Me 1

579. Et Me Me 2

580. Et Me Me 0

581. Et Me Me 1

582. Et Me Me 2

583. Et Me Me 0

584. Et Me Me 1

585. Et Me Me 2

586. Et Me Me 0

587. Et Me Me 1

588. Et Me Me 2

589. Et Me Me 0

590. Et Me Me 1

591. Et Me Me 2

592. Et Me Me 0 CHOC₂H₄F 593. Et Me Me 1 CHOC₂H₄F 594. Et Me Me 2CHOC₂H₄F 595. Et Me Me 0 C═NOMe 596. Et Me Me 1 C═NOMe 597. Et Me Me 2C═NOMe 598. Et Me Me 0 C═NOCH₂CCH 599. Et Me Me 1 C═NOCH₂CCH 600. Et MeMe 2 C═NOCH₂CCH 601. Et Me Me 0 C═NOCH₂CH═CH₂ 602. Et Me Me 1C═NOCH₂CH═CH₂ 603. Et Me Me 2 C═NOCH₂CH═CH₂ 604. Et Me Me 0 C═O 605. EtMe Me 1 C═O 606. Et Me Me 2 C═O 607. Et Me Me 0 C═S 608. Et Me Me 1 C═S609. Et Me Me 2 C═S 610. Et Me Me 0 C═S 611. Et Me Me 1 C═S 612. Et MeMe 2 C═S 613. Et Me Me 0 C═N—N(CH₃)₂ 614. Et Me Me 1 C═N—N(CH₃)₂ 615. EtMe Me 2 C═N—N(CH₃)₂ 616. Et Me Me 0 O 617. Et Me Me 1 O 618. Et Me Me 2O 619. Et Me Me 0 S 620. Et Me Me 1 S 621. Et Me Me 2 S 622. Et Me Me 0SO 623. Et Me Me 1 SO 624. Et Me Me 2 SO 625. Et Me Me 0 SO₂ 626. Et MeMe 1 SO₂ 627. Et Me Me 2 SO₂ 628. Et Me Me 0 NMe 629. Et Me Me 1 NMe630. Et Me Me 2 NMe 631. Et Me H 0 CH₂ 632. Et Me H 1 CH₂ 633. Et Me H 2CH₂ 634. Et Me H 0 CHMe 635. Et Me H 1 CHMe 636. Et Me H 2 CHMe 637. EtMe H 0 C(CH₃)₂ 638. Et Me H 1 C(CH₃)₂ 639. Et Me H 2 C(CH₃)₂ 640. Et MeH 0 C(OC₂H₄O) 641. Et Me H 1 C(OC₂H₄O) 642. Et Me H 2 C(OC₂H₄O) 643. EtMe H 0 C(SC₂H₄S) 644. Et Me H 1 C(SC₂H₄S) 645. Et Me H 2 C(SC₂H₄S) 646.Et Me H 0 CHOMe 647. Et Me H 1 CHOMe 648. Et Me H 2 CHOMe 649. Et Me H 0CHOEt 650. Et Me H 1 CHOEt 651. Et Me H 2 CHOEt 652. Et Me H 0 CHOiPr653. Et Me H 1 CHOiPr 654. Et Me H 2 CHOiPr 655. Et Me H 0 CHOCH₂cPr656. Et Me H 1 CHOCH₂cPr 657. Et Me H 2 CHOCH₂cPr 658. Et Me H 0CHOC₂H₄OMe 659. Et Me H 1 CHOC₂H₄OMe 660. Et Me H 2 CHOC₂H₄OMe 661. EtMe H 0 CHOCH₂CCH 662. Et Me H 1 CHOCH₂CCH 663. Et Me H 2 CHOCH₂CCH 664.Et Me H 0 CHOCH₂CH═CH₂ 665. Et Me H 1 CHOCH₂CH═CH₂ 666. Et Me H 2CHOCH₂CH═CH₂ 667. Et Me H 0

668. Et Me H 1

669. Et Me H 2

670. Et Me H 0

671. Et Me H 1

672. Et Me H 2

673. Et Me H 0

674. Et Me H 1

675. Et Me H 2

676. Et Me H 0

677. Et Me H 1

678. Et Me H 2

679. Et Me H 0

680. Et Me H 1

681. Et Me H 2

682. Et Me H 0 CHOC₂H₄F 683. Et Me H 1 CHOC₂H₄F 684. Et Me H 2 CHOC₂H₄F685. Et Me H 0 C═NOMe 686. Et Me H 1 C═NOMe 687. Et Me H 2 C═NOMe 688.Et Me H 0 C═NOCH₂CCH 689. Et Me H 1 C═NOCH₂CCH 690. Et Me H 2 C═NOCH₂CCH691. Et Me H 0 C═NOCH₂CH═CH₂ 692. Et Me H 1 C═NOCH₂CH═CH₂ 693. Et Me H 2C═NOCH₂CH═CH₂ 694. Et Me H 0 C═O 695. Et Me H 1 C═O 696. Et Me H 2 C═O697. Et Me H 0 C═S 698. Et Me H 1 C═S 699. Et Me H 2 C═S 700. Et Me H 0C═S 701. Et Me H 1 C═S 702. Et Me H 2 C═S 703. Et Me H 0 C═N—N(CH₃)₂704. Et Me H 1 C═N—N(CH₃)₂ 705. Et Me H 2 C═N—N(CH₃)₂ 706. Et Me H 0 O707. Et Me H 1 O 708. Et Me H 2 O 709. Et Me H 0 S 710. Et Me H 1 S 711.Et Me H 2 S 712. Et Me H 0 SO 713. Et Me H 1 SO 714. Et Me H 2 SO 715.Et Me H 0 SO₂ 716. Et Me H 1 SO₂ 717. Et Me H 2 SO₂ 718. Et Me H 0 NMe719. Et Me H 1 NMe 720. Et Me H 2 NMe

TABLE 3 Inventive compounds of the general formula (I) in which Q is Q3,Y is S(O)_(m), R⁵ is hydrogen and n is 2

No. R² R³ R⁴ m X 1H NMR  721. Me Me Me 0 CH₂  722. Me Me Me 1 CH₂  723.Me Me Me 2 CH₂  724. Me Me Me 0 CHMe  725. Me Me Me 1 CHMe  726. Me MeMe 2 CHMe  727. Me Me Me 0 C(CH₃)₂  728. Me Me Me 1 C(CH₃)₂  729. Me MeMe 2 C(CH₃)₂  730. Me Me Me 0 C(OC₂H₄O)  731. Me Me Me 1 C(OC₂H₄O)  732.Me Me Me 2 C(OC₂H₄O)  733. Me Me Me 0 C(SC₂H₄S)  734. Me Me Me 1C(SC₂H₄S)  735. Me Me Me 2 C(SC₂H₄S)  736. Me Me Me 0 CHOMe  737. Me MeMe 1 CHOMe  738. Me Me Me 2 CHOMe  739. Me Me Me 0 CHOEt  740. Me Me Me1 CHOEt  741. Me Me Me 2 CHOEt  742. Me Me Me 0 CHOiPr  743. Me Me Me 1CHOiPr  744. Me Me Me 2 CHOiPr  745. Me Me Me 0 CHOCH₂cPr  746. Me Me Me1 CHOCH₂cPr  747. Me Me Me 2 CHOCH₂cPr  748. Me Me Me 0 CHOC₂H₄OMe  749.Me Me Me 1 CHOC₂H₄OMe  750. Me Me Me 2 CHOC₂H₄OMe  751. Me Me Me 0CHOCH₂CCH  752. Me Me Me 1 CHOCH₂CCH  753. Me Me Me 2 CHOCH₂CCH  754. MeMe Me 0 CHOCH₂CH═CH₂  755. Me Me Me 1 CHOCH₂CH═CH₂  756. Me Me Me 2CHOCH₂CH═CH₂  757. Me Me Me 0

 758. Me Me Me 1

 759. Me Me Me 2

 760. Me Me Me 0

 761. Me Me Me 1

 762. Me Me Me 2

DMSO-d₆, 400 MHz: 11.42 (s, 1H), 8.39 (s, 1H), 8.35-8.30 (m, 2H), 7.70(s, 1H), 6.52 (dd, 1H), 3.79- 3.69 (m, 1H), 3.61- 3.52 (m, 1H), 2.80-2.60 (m, 5H), 2.38 (s, 3H), 2.21 (s, 3H)  763. Me Me Me 0

 764. Me Me Me 1

 765. Me Me Me 2

 766. Me Me Me 0

 767. Me Me Me 1

 768. Me Me Me 2

 769. Me Me Me 0

 770. Me Me Me 1

 771. Me Me Me 2

 772. Me Me Me 0 CHOC₂H₄F  773. Me Me Me 1 CHOC₂H₄F  774. Me Me Me 2CHOC₂H₄F  775. Me Me Me 0 C═NOMe  776. Me Me Me 1 C═NOMe  777. Me Me Me2 C═NOMe  778. Me Me Me 0 C═NOCH₂CCH  779. Me Me Me 1 C═NOCH₂CCH  780.Me Me Me 2 C═NOCH₂CCH  781. Me Me Me 0 C═NOCH₂CH═CH₂  782. Me Me Me 1C═NOCH₂CH═CH₂  783. Me Me Me 2 C═NOCH₂CH═CH₂  784. Me Me Me 0 C═O  785.Me Me Me 1 C═O  786. Me Me Me 2 C═O  787. Me Me Me 0 C═S  788. Me Me Me1 C═S  789. Me Me Me 2 C═S  790. Me Me Me 0 C═S  791. Me Me Me 1 C═S 792. Me Me Me 2 C═S  793. Me Me Me 0 C═N—N(CH₃)₂  794. Me Me Me 1C═N—N(CH₃)₂  795. Me Me Me 2 C═N—N(CH₃)₂  796. Me Me Me 0 O  797. Me MeMe 1 O  798. Me Me Me 2 O  799. Me Me Me 0 S  800. Me Me Me 1 S  801. MeMe Me 2 S  802. Me Me Me 0 SO  803. Me Me Me 1 SO  804. Me Me Me 2 SO 805. Me Me Me 0 SO₂  806. Me Me Me 1 SO₂  807. Me Me Me 2 SO₂  808. MeMe Me 0 NMe  809. Me Me Me 1 NMe  810. Me Me Me 2 NMe  811. Me Me H 0CH₂  812. Me Me H 1 CH₂  813. Me Me H 2 CH₂  814. Me Me H 0 CHMe  815.Me Me H 1 CHMe  816. Me Me H 2 CHMe  817. Me Me H 0 C(CH₃)₂  818. Me MeH 1 C(CH₃)₂  819. Me Me H 2 C(CH₃)₂  820. Me Me H 0 C(OC₂H₄O)  821. MeMe H 1 C(OC₂H₄O)  822. Me Me H 2 C(OC₂H₄O)  823. Me Me H 0 C(SC₂H₄S) 824. Me Me H 1 C(SC₂H₄S)  825. Me Me H 2 C(SC₂H₄S)  826. Me Me H 0CHOMe  827. Me Me H 1 CHOMe  828. Me Me H 2 CHOMe  829. Me Me H 0 CHOEt 830. Me Me H 1 CHOEt  831. Me Me H 2 CHOEt  832. Me Me H 0 CHOiPr  833.Me Me H 1 CHOiPr  834. Me Me H 2 CHOiPr  835. Me Me H 0 CHOCH₂cPr  836.Me Me H 1 CHOCH₂cPr  837. Me Me H 2 CHOCH₂cPr  838. Me Me H 0 CHOC₂H₄OMe 839. Me Me H 1 CHOC₂H₄OMe  840. Me Me H 2 CHOC₂H₄OMe  841. Me Me H 0CHOCH₂CCH  842. Me Me H 1 CHOCH₂CCH  843. Me Me H 2 CHOCH₂CCH  844. MeMe H 0 CHOCH₂CH═CH₂  845. Me Me H 1 CHOCH₂CH═CH₂  846. Me Me H 2CHOCH₂CH═CH₂  847. Me Me H 0

 848. Me Me H 1

 849. Me Me H 2

 850. Me Me H 0

 851. Me Me H 1

 852. Me Me H 2

 853. Me Me H 0

 854. Me Me H 1

 855. Me Me H 2

 856. Me Me H 0

 857. Me Me H 1

 858. Me Me H 2

 859. Me Me H 0

 860. Me Me H 1

 861. Me Me H 2

 862. Me Me H 0 CHOC₂H₄F  863. Me Me H 1 CHOC₂H₄F  864. Me Me H 2CHOC₂H₄F  865. Me Me H 0 C═NOMe  866. Me Me H 1 C═NOMe  867. Me Me H 2C═NOMe  868. Me Me H 0 C═NOCH₂CCH  869. Me Me H 1 C═NOCH₂CCH  870. Me MeH 2 C═NOCH₂CCH  871. Me Me H 0 C═NOCH₂CH═CH₂  872. Me Me H 1C═NOCH₂CH═CH₂  873. Me Me H 2 C═NOCH₂CH═CH₂  874. Me Me H 0 C═O  875. MeMe H 1 C═O  876. Me Me H 2 C═O  877. Me Me H 0 C═S  878. Me Me H 1 C═S 879. Me Me H 2 C═S  880. Me Me H 0 C═S  881. Me Me H 1 C═S  882. Me MeH 2 C═S  883. Me Me H 0 C═N—N(CH₃)₂  884. Me Me H 1 C═N—N(CH₃)₂  885. MeMe H 2 C═N—N(CH₃)₂  886. Me Me H 0 O  887. Me Me H 1 O  888. Me Me H 2 O 889. Me Me H 0 S  890. Me Me H 1 S  891. Me Me H 2 S  892. Me Me H 0 SO 893. Me Me H 1 SO  894. Me Me H 2 SO  895. Me Me H 0 SO₂  896. Me Me H1 SO₂  897. Me Me H 2 SO₂  898. Me Me H 0 NMe  899. Me Me H 1 NMe  900.Me Me H 2 NMe  901. Et Me Me 0 CH₂  902. Et Me Me 1 CH₂  903. Et Me Me 2CH₂  904. Et Me Me 0 CHMe  905. Et Me Me 1 CHMe  906. Et Me Me 2 CHMe 907. Et Me Me 0 C(CH₃)₂  908. Et Me Me 1 C(CH₃)₂  909. Et Me Me 2C(CH₃)₂  910. Et Me Me 0 C(OC₂H₄O)  911. Et Me Me 1 C(OC₂H₄O)  912. EtMe Me 2 C(OC₂H₄O)  913. Et Me Me 0 C(SC₂H₄S)  914. Et Me Me 1 C(SC₂H₄S) 915. Et Me Me 2 C(SC₂H₄S)  916. Et Me Me 0 CHOMe  917. Et Me Me 1 CHOMe 918. Et Me Me 2 CHOMe  919. Et Me Me 0 CHOEt  920. Et Me Me 1 CHOEt 921. Et Me Me 2 CHOEt  922. Et Me Me 0 CHOiPr  923. Et Me Me 1 CHOiPr 924. Et Me Me 2 CHOiPr  925. Et Me Me 0 CHOCH₂cPr  926. Et Me Me 1CHOCH₂cPr  927. Et Me Me 2 CHOCH₂cPr  928. Et Me Me 0 CHOC₂H₄OMe  929.Et Me Me 1 CHOC₂H₄OMe  930. Et Me Me 2 CHOC₂H₄OMe  931. Et Me Me 0CHOCH₂CCH  932. Et Me Me 1 CHOCH₂CCH  933. Et Me Me 2 CHOCH₂CCH  934. EtMe Me 0 CHOCH₂CH═CH₂  935. Et Me Me 1 CHOCH₂CH═CH₂  936. Et Me Me 2CHOCH₂CH═CH₂  937. Et Me Me 0

 938. Et Me Me 1

 939. Et Me Me 2

 940. Et Me Me 0

 941. Et Me Me 1

 942. Et Me Me 2

DMSO-d₆, 400 MHz: 11.35 (s, 1H), 8.39 (s, 1H), 8.34-8.30 (m, 2H), 7.67(s, 1H), 6.52 (dd, 1H), 3.80- 3.71 (m, 1H), 3.60- 3.53 (m, 1H), 2.82-2.60 (m, 7H), 2.20 (s, 3H), 1.26 (t, 3H)  943. Et Me Me 0

 944. Et Me Me 1

 945. Et Me Me 2

 946. Et Me Me 0

 947. Et Me Me 1

 948. Et Me Me 2

 949. Et Me Me 0

 950. Et Me Me 1

 951. Et Me Me 2

 952. Et Me Me 0 CHOC₂H₄F  953. Et Me Me 1 CHOC₂H₄F  954. Et Me Me 2CHOC₂H₄F  955. Et Me Me 0 C═NOMe  956. Et Me Me 1 C═NOMe  957. Et Me Me2 C═NOMe  958. Et Me Me 0 C═NOCH₂CCH  959. Et Me Me 1 C═NOCH₂CCH  960.Et Me Me 2 C═NOCH₂CCH  961. Et Me Me 0 C═NOCH₂CH═CH₂  962. Et Me Me 1C═NOCH₂CH═CH₂  963. Et Me Me 2 C═NOCH₂CH═CH₂  964. Et Me Me 0 C═O  965.Et Me Me 1 C═O  966. Et Me Me 2 C═O  967. Et Me Me 0 C═S  968. Et Me Me1 C═S  969. Et Me Me 2 C═S  970. Et Me Me 0 C═S  971. Et Me Me 1 C═S 972. Et Me Me 2 C═S  973. Et Me Me 0 C═N—N(CH₃)₂  974. Et Me Me 1C═N—N(CH₃)₂  975. Et Me Me 2 C═N—N(CH₃)₂  976. Et Me Me 0 O  977. Et MeMe 1 O  978. Et Me Me 2 O  979. Et Me Me 0 S  980. Et Me Me 1 S  981. EtMe Me 2 S  982. Et Me Me 0 SO  983. Et Me Me 1 SO  984. Et Me Me 2 SO 985. Et Me Me 0 SO₂  986. Et Me Me 1 SO₂  987. Et Me Me 2 SO₂  988. EtMe Me 0 NMe  989. Et Me Me 1 NMe  990. Et Me Me 2 NMe  991. Et Me H 0CH₂  992. Et Me H 1 CH₂  993. Et Me H 2 CH₂  994. Et Me H 0 CHMe  995.Et Me H 1 CHMe  996. Et Me H 2 CHMe  997. Et Me H 0 C(CH₃)₂  998. Et MeH 1 C(CH₃)₂  999. Et Me H 2 C(CH₃)₂ 1000 Et Me H 0 C(OC₂H₄O) 1001 Et MeH 1 C(OC₂H₄O) 1002 Et Me H 2 C(OC₂H₄O) 1003 Et Me H 0 C(SC₂H₄S) 1004 EtMe H 1 C(SC₂H₄S) 1005 Et Me H 2 C(SC₂H₄S) 1006 Et Me H 0 CHOMe 1007 EtMe H 1 CHOMe 1008 Et Me H 2 CHOMe 1009 Et Me H 0 CHOEt 1010 Et Me H 1CHOEt 1011 Et Me H 2 CHOEt 1012 Et Me H 0 CHOiPr 1013 Et Me H 1 CHOiPr1014 Et Me H 2 CHOiPr 1015 Et Me H 0 CHOCH₂cPr 1016 Et Me H 1 CHOCH₂cPr1017 Et Me H 2 CHOCH₂cPr 1018 Et Me H 0 CHOC₂H₄OMe 1019 Et Me H 1CHOC₂H₄OMe 1020 Et Me H 2 CHOC₂H₄OMe 1021 Et Me H 0 CHOCH₂CCH 1022 Et MeH 1 CHOCH₂CCH 1023 Et Me H 2 CHOCH₂CCH 1024 Et Me H 0 CHOCH₂CH═CH₂ 1025Et Me H 1 CHOCH₂CH═CH₂ 1026 Et Me H 2 CHOCH₂CH═CH₂ 1027 Et Me H 0

1028 Et Me H 1

1029 Et Me H 2

1030 Et Me H 0

1031 Et Me H 1

1032 Et Me H 2

1033 Et Me H 0

1034 Et Me H 1

1035 Et Me H 2

1036 Et Me H 0

1037 Et Me H 1

1038 Et Me H 2

1039 Et Me H 0

1040 Et Me H 1

1041 Et Me H 2

1042 Et Me H 0 CHOC₂H₄F 1043 Et Me H 1 CHOC₂H₄F 1044 Et Me H 2 CHOC₂H₄F1045 Et Me H 0 C═NOMe 1046 Et Me H 1 C═NOMe 1047 Et Me H 2 C═NOMe 1048Et Me H 0 C═NOCH₂CCH 1049 Et Me H 1 C═NOCH₂CCH 1050 Et Me H 2 C═NOCH₂CCH1051 Et Me H 0 C═NOCH₂CH═CH₂ 1052 Et Me H 1 C═NOCH₂CH═CH₂ 1053 Et Me H 2C═NOCH₂CH═CH₂ 1054 Et Me H 0 C═O 1055 Et Me H 1 C═O 1056 Et Me H 2 C═O1057 Et Me H 0 C═S 1058 Et Me H 1 C═S 1059 Et Me H 2 C═S 1060 Et Me H 0C═S 1061 Et Me H 1 C═S 1062 Et Me H 2 C═S 1063 Et Me H 0 C═N—N(CH₃)₂1064 Et Me H 1 C═N—N(CH₃)₂ 1065 Et Me H 2 C═N—N(CH₃)₂ 1066 Et Me H 0 O1067 Et Me H 1 O 1068 Et Me H 2 O 1069 Et Me H 0 S 1070 Et Me H 1 S 1071Et Me H 2 S 1072 Et Me H 0 SO 1073 Et Me H 1 SO 1074 Et Me H 2 SO 1075Et Me H 0 SO₂ 1076 Et Me H 1 SO₂ 1077 Et Me H 2 SO₂ 1078 Et Me H 0 NMe1079 Et Me H 1 NMe 1080 Et Me H 2 NMe

TABLE 4 Inventive compounds of the general formula (I) in which Q is Q1,R⁵ is hydrogen and n is 1

No. R¹ R³ R⁴ Y X 1H NMR 1081. Me Me Me S CH₂ 1082. Me Me Me SO CH₂ 1083.Me Me Me SO₂ CH₂ 1084. Me Me Me S CHMe 1085. Me Me Me SO CHMe 1086. MeMe Me SO₂ CHMe 1087. Me Me Me S C(CH₃)₂ 1088. Me Me Me SO C(CH₃)₂ 1089.Me Me Me SO₂ C(CH₃)₂ 1090. Me Me Me S C(OC₂H₄O) 1091. Me Me Me SOC(OC₂H₄O) 1092. Me Me Me SO₂ C(OC₂H₄O) 1093. Me Me Me S C(SC₂H₄S) 1094.Me Me Me SO C(SC₂H₄S) 1095. Me Me Me SO₂ C(SC₂H₄S) 1096. Me Me Me SCHOMe 1097. Me Me Me SO CHOMe 1098. Me Me Me SO₂ CHOMe 1099. Me Me Me SCHOEt 1100. Me Me Me SO CHOEt 1101. Me Me Me SO₂ CHOEt 1102. Me Me Me SCHOiPr 1103. Me Me Me SO CHOiPr 1104. Me Me Me SO₂ CHOiPr 1105. Me Me MeS CHOCH₂cPr 1106. Me Me Me SO CHOCH₂cPr 1107. Me Me Me SO₂ CHOCH₂cPr1108. Me Me Me S CHOC₂H₄OMe 1109. Me Me Me SO CHOC₂H₄OMe 1110. Me Me MeSO₂ CHOC₂H₄OMe 1111. Me Me Me S CHOCH₂CCH 1112. Me Me Me SO CHOCH₂CCH1113. Me Me Me SO₂ CHOCH₂CCH 1114. Me Me Me S CHOCH₂CH═CH₂ 1115. Me MeMe SO CHOCH₂CH═CH₂ 1116. Me Me Me SO₂ CHOCH₂CH═CH₂ 1117. Me Me Me S

1118. Me Me Me SO

1119. Me Me Me SO₂

1120. Me Me Me S

1121. Me Me Me SO

1122. Me Me Me SO₂

1123. Me Me Me S

1124. Me Me Me SO

1125. Me Me Me SO₂

1126. Me Me Me S

1127. Me Me Me SO

1128. Me Me Me SO₂

1129. Me Me Me S

1130. Me Me Me SO

1131. Me Me Me SO₂

1132. Me Me Me S CHOC₂H₄F 1133. Me Me Me SO CHOC₂H₄F 1134. Me Me Me SO₂CHOC₂H₄F 1135. Me Me Me S C═NOMe 1136. Me Me Me SO C═NOMe 1137. Me Me MeSO₂ C═NOMe 1138. Me Me Me S C═NOCH₂CCH 1139. Me Me Me SO C═NOCH₂CCH1140. Me Me Me SO₂ C═NOCH₂CCH 1141. Me Me Me S C═NOCH₂CH═CH₂ 1142. Me MeMe SO C═NOCH₂CH═CH₂ 1143. Me Me Me SO₂ C═NOCH₂CH═CH₂ 1144. Me Me Me SC═O 1145. Me Me Me SO C═O 1146. Me Me Me SO₂ C═O 1147. Me Me Me S C═S1148. Me Me Me SO C═S 1149. Me Me Me SO₂ C═S 1150. Me Me Me S C═S 1151.Me Me Me SO C═S 1152. Me Me Me SO₂ C═S 1153. Me Me Me S C═N—N(CH₃)₂1154. Me Me Me SO C═N—N(CH₃)₂ 1155. Me Me Me SO₂ C═N—N(CH₃)₂ 1156. Me MeMe S O 1157. Me Me Me SO O 1158. Me Me Me SO₂ O 1159. Me Me Me S S 1160.Me Me Me SO S 1161. Me Me Me SO₂ S 1162. Me Me Me S SO 1163. Me Me Me SOSO 1164. Me Me Me SO₂ SO 1165. Me Me Me S SO₂ 1166. Me Me Me SO SO₂1167. Me Me Me SO₂ SO₂ 1168. Me Me Me S NMe 1169. Me Me Me SO NMe 1170.Me Me Me SO₂ NMe 1171. Me Me Me O O 1172. Me Me H O O DMSO-d6, 400 MHz:11.33 (s, 1H), 7.34 (d, 1H), 6.92 (d, 1H), 6.12 (s, 2H), 3.93 (s, 3H),2.30 (s, 3H) 1173. Me SMe H O O DMSO-d6, 400 MHz: 11.50 (bs, 1H), 7.21(d, 1H), 6.99 (d, 1H), 6.18 (s, 2H), 3.96 (s, 3H), 2.44 (s, 3H) 1174. MeCl H O O 1175. Me Cl H S CH₂ 1176. Me Cl H SO CH₂ 1177. Me Cl H SO₂ CH₂DMSO, 400 MHz: 3.41 (t, 2H), 3.76 (t, 2H), 4.02 (s, 3H), 7.94 (s, 2H),11.95 (s, 1H) 1178. Me Cl H S CHMe 1179. Me Cl H SO CHMe 1180. Me Cl HSO₂ CHMe 1181. Me Cl H S C(CH₃)₂ 1182. Me Cl H SO C(CH₃)₂ 1183. Me Cl HSO₂ C(CH₃)₂ 1184. Me Cl H S C(OC₂H₄O) 1185. Me Cl H SO C(OC₂H₄O) 1186.Me Cl H SO₂ C(OC₂H₄O) 1187. Me Cl H S C(SC₂H₄S) 1188. Me Cl H SOC(SC₂H₄S) 1189. Me Cl H SO₂ C(SC₂H₄S) 1190. Me Cl H S CHOMe 1191. Me ClH SO CHOMe 1192. Me Cl H SO₂ CHOMe CDCl3, 400 MHz: 3.57 (s, 3H), 3.68(dd, 1H), 3.81 (d, 1H), 4.13 (s, 3H), 5.25 (d, 1H), 7.80 (d, 1H), 7.98(d, 1H), 9.85 (s, 1H) 1193. Me Cl H S CHOEt 1194. Me Cl H SO CHOEt 1195.Me Cl H SO₂ CHOEt 1196. Me Cl H S CHOiPr 1197. Me Cl H SO CHOiPr 1198.Me Cl H SO₂ CHOiPr 1199. Me Cl H S CHOCH₂cPr 1200. Me Cl H SO CHOCH₂cPr1201. Me Cl H SO₂ CHOCH₂cPr 1202. Me Cl H S CHOC₂H₄OMe 1203. Me Cl H SOCHOC₂H₄OMe 1204. Me Cl H SO₂ CHOC₂H₄OMe 1205. Me Cl H S CHOCH₂CCH 1206.Me Cl H SO CHOCH₂CCH 1207. Me Cl H SO₂ CHOCH₂CCH 1208. Me Cl H SCHOCH₂CH═CH₂ 1209. Me Cl H SO CHOCH₂CH═CH₂ 1210. Me Cl H SO₂CHOCH₂CH═CH₂ 1211. Me Cl H S

1212. Me Cl H SO

1213. Me Cl H SO₂

1214. Me Cl H S

1215. Me Cl H SO

1216. Me Cl H SO₂

1217. Me Cl H S

1218. Me Cl H SO

1219. Me Cl H SO₂

1220. Me Cl H S

1221. Me Cl H SO

1222. Me Cl H SO₂

1223. Me Cl H S

1224. Me Cl H SO

1225. Me Cl H SO₂

1226. Me Cl H S CHOC₂H₄F 1227. Me Cl H SO CHOC₂H₄F 1228. Me Cl H SO₂CHOC₂H₄F 1229. Me Cl H S C═NOMe 1230. Me Cl H SO C═NOMe 1231. Me Cl HSO₂ C═NOMe 1232. Me Cl H S C═NOCH₂CCH 1233. Me Cl H SO C═NOCH₂CCH 1234.Me Cl H SO₂ C═NOCH₂CCH 1235. Me Cl H S C═NOCH₂CH═CH₂ 1236. Me Cl H SOC═NOCH₂CH═CH₂ 1237. Me Cl H SO₂ C═NOCH₂CH═CH₂ 1238. Me Cl H S C═O 1239.Me Cl H SO C═O 1240. Me Cl H SO₂ C═O 1241. Me Cl H S C═S 1242. Me Cl HSO C═S 1243. Me Cl H SO₂ C═S 1244. Me Cl H S C═S 1245. Me Cl H SO C═S1246. Me Cl H SO₂ C═S 1247. Me Cl H S C═N—N(CH₃)₂ 1248. Me Cl H SOC═N—N(CH₃)₂ 1249. Me Cl H SO₂ C═N—N(CH₃)₂ 1250. Me Cl H S O 1251. Me ClH SO O 1252. Me Cl H SO₂ O 1253. Me Cl H S S 1254. Me Cl H SO S 1255. MeCl H SO₂ S 1256. Me Cl H S SO 1257. Me Cl H SO SO 1258. Me Cl H SO₂ SO1259. Me Cl H S SO₂ 1260. Me Cl H SO SO₂ 1261. Me Cl H SO₂ SO₂ 1262. MeCl H S NMe 1263. Me Cl H SO NMe 1264. Me Cl H SO₂ NMe 1265. Et Me Me SCH₂ 1266. Et Me Me SO CH₂ 1267. Et Me Me SO₂ CH₂ 1268. Et Me Me S CHMe1269. Et Me Me SO CHMe 1270. Et Me Me SO₂ CHMe 1271. Et Me Me S C(CH₃)₂1272. Et Me Me SO C(CH₃)₂ 1273. Et Me Me SO₂ C(CH₃)₂ 1274. Et Me Me SC(OC₂H₄O) 1275. Et Me Me SO C(OC₂H₄O) 1276. Et Me Me SO₂ C(OC₂H₄O) 1277.Et Me Me S C(SC₂H₄S) 1278. Et Me Me SO C(SC₂H₄S) 1279. Et Me Me SO₂C(SC₂H₄S) 1280. Et Me Me S CHOMe 1281. Et Me Me SO CHOMe 1282. Et Me MeSO₂ CHOMe 1283. Et Me Me S CHOEt 1284. Et Me Me SO CHOEt 1285. Et Me MeSO₂ CHOEt 1286. Et Me Me S CHOiPr 1287. Et Me Me SO CHOiPr 1288. Et MeMe SO₂ CHOiPr 1289. Et Me Me S CHOCH₂cPr 1290. Et Me Me SO CHOCH₂cPr1291. Et Me Me SO₂ CHOCH₂cPr 1292. Et Me Me S CHOC₂H₄OMe 1293. Et Me MeSO CHOC₂H₄OMe 1294. Et Me Me SO₂ CHOC₂H₄OMe 1295. Et Me Me S CHOCH₂CCH1296. Et Me Me SO CHOCH₂CCH 1297. Et Me Me SO₂ CHOCH₂CCH 1298. Et Me MeS CHOCH₂CH═CH₂ 1299. Et Me Me SO CHOCH₂CH═CH₂ 1300. Et Me Me SO₂CHOCH₂CH═CH₂ 1301. Et Me Me S

1302. Et Me Me SO

1303. Et Me Me SO₂

1304. Et Me Me S

1305. Et Me Me SO

1306. Et Me Me SO₂

1307. Et Me Me S

1308. Et Me Me SO

1309. Et Me Me SO₂

1310. Et Me Me S

1311. Et Me Me SO

1312. Et Me Me SO₂

1313. Et Me Me S

1314. Et Me Me SO

1315. Et Me Me SO₂

1316. Et Me Me S CHOC₂H₄F 1317. Et Me Me SO CHOC₂H₄F 1318. Et Me Me SO₂CHOC₂H₄F 1319. Et Me Me S C═NOMe 1320. Et Me Me SO C═NOMe 1321. Et Me MeSO₂ C═NOMe 1322. Et Me Me S C═NOCH₂CCH 1323. Et Me Me SO C═NOCH₂CCH1324. Et Me Me SO₂ C═NOCH₂CCH 1325. Et Me Me S C═NOCH₂CH═CH₂ 1326. Et MeMe SO C═NOCH₂CH═CH₂ 1327. Et Me Me SO₂ C═NOCH₂CH═CH₂ 1328. Et Me Me SC═O 1329. Et Me Me SO C═O 1330. Et Me Me SO₂ C═O 1331. Et Me Me S C═S1332. Et Me Me SO C═S 1333. Et Me Me SO₂ C═S 1334. Et Me Me S C═S 1335.Et Me Me SO C═S 1336. Et Me Me SO₂ C═S 1337. Et Me Me S C═N—N(CH₃)₂1338. Et Me Me SO C═N—N(CH₃)₂ 1339. Et Me Me SO₂ C═N—N(CH₃)₂ 1340. Et MeMe S O 1341. Et Me Me SO O 1342. Et Me Me SO₂ O 1343. Et Me Me S S 1344.Et Me Me SO S 1345. Et Me Me SO₂ S 1346. Et Me Me S SO 1347. Et Me Me SOSO 1348. Et Me Me SO₂ SO 1349. Et Me Me S SO₂ 1350. Et Me Me SO SO₂1351. Et Me Me SO₂ SO₂ 1352. Et Me Me S NMe 1353. Et Me Me SO NMe 1354.Et Me Me SO₂ NMe 1355. Et Me Me O O 1356. Et Me H O O CDCl3, 400 MHz:9.65 (s, 1H), 7.42 (d, 1H), 6.79 (d, 1H), 6.06 (s, 2H), 4.43 (q, 2H),2.41 (s, 3H), 1.60 (t, 3H) 1357. Et SMe H O O 1358. Et Cl H O O 1359. EtCl H S CH₂ 1360. Et Cl H SO CH₂ 1361. Et Cl H SO₂ CH₂ DMSO, 400 MHz:1.48 (t, 3H), 3.42 (t, 2H), 3.75 (t, 2H), 4.38 (q, 2H), 7.93 (s, 2H),11.86 (s, 1H) 1362. Et Cl H S CHMe 1363. Et Cl H SO CHMe 1364. Et Cl HSO₂ CHMe 1365. Et Cl H S C(CH₃)₂ 1366. Et Cl H SO C(CH₃)₂ 1367. Et Cl HSO₂ C(CH₃)₂ 1368. Et Cl H S C(OC₂H₄O) 1369. Et Cl H SO C(OC₂H₄O) 1370.Et Cl H SO₂ C(OC₂H₄O) 1371. Et Cl H S C(SC₂H₄S) 1372. Et Cl H SOC(SC₂H₄S) 1373. Et Cl H SO₂ C(SC₂H₄S) 1374. Et Cl H S CHOMe 1375. Et ClH SO CHOMe 1376. Et Cl H SO₂ CHOMe CDCl3, 400 MHz: 1.62 (t, 3H), 3.55(s, 3H), 3.66 (dd, 1H), 3.81 (d, 1H), 4.47 (q, 2H), 5.23 (d, 1H), 7.75(d, 1H), 7.94 (d, 1H), 10.6 (s, 1H) 1377. Et Cl H S CHOEt 1378. Et Cl HSO CHOEt 1379. Et Cl H SO₂ CHOEt 1380. Et Cl H S CHOiPr 1381. Et Cl H SOCHOiPr 1382. Et Cl H SO₂ CHOiPr 1383. Et Cl H S CHOCH₂cPr 1384. Et Cl HSO CHOCH₂cPr 1385. Et Cl H SO₂ CHOCH₂cPr 1386. Et Cl H S CHOC₂H₄OMe1387. Et Cl H SO CHOC₂H₄OMe 1388. Et Cl H SO₂ CHOC₂H₄OMe 1389. Et Cl H SCHOCH₂CCH 1390. Et Cl H SO CHOCH₂CCH 1391. Et Cl H SO₂ CHOCH₂CCH 1392.Et Cl H S CHOCH₂CH═CH₂ 1393. Et Cl H SO CHOCH₂CH═CH₂ 1394. Et Cl H SO₂CHOCH₂CH═CH₂ 1395. Et Cl H S

1396. Et Cl H SO

1397. Et Cl H SO₂

1398. Et Cl H S

1399. Et Cl H SO

1400. Et Cl H SO₂

1401. Et Cl H S

1402. Et Cl H SO

1403. Et Cl H SO₂

1404. Et Cl H S

1405. Et Cl H SO

1406. Et Cl H SO₂

1407. Et Cl H S

1408. Et Cl H SO

1409. Et Cl H SO₂

1410. Et Cl H S CHOC₂H₄F 1411. Et Cl H SO CHOC₂H₄F 1412. Et Cl H SO₂CHOC₂H₄F 1413. Et Cl H S C═NOMe 1414. Et Cl H SO C═NOMe 1415. Et Cl HSO₂ C═NOMe 1416. Et Cl H S C═NOCH₂CCH 1417. Et Cl H SO C═NOCH₂CCH 1418.Et Cl H SO₂ C═NOCH₂CCH 1419. Et Cl H S C═NOCH₂CH═CH₂ 1420. Et Cl H SOC═NOCH₂CH═CH₂ 1421. Et Cl H SO₂ C═NOCH₂CH═CH₂ 1422. Et Cl H S C═O 1423.Et Cl H SO C═O 1424. Et Cl H SO₂ C═O 1425. Et Cl H S C═S 1426. Et Cl HSO C═S 1427. Et Cl H SO₂ C═S 1428. Et Cl H S C═S 1429. Et Cl H SO C═S1430. Et Cl H SO₂ C═S 1431. Et Cl H S C═N—N(CH₃)₂ 1432. Et Cl H SOC═N—N(CH₃)₂ 1433. Et Cl H SO₂ C═N—N(CH₃)₂ 1434. Et Cl H S O 1435. Et ClH SO O 1436. Et Cl H SO₂ O 1437. Et Cl H S S 1438. Et Cl H SO S 1439. EtCl H SO₂ S 1440. Et Cl H S SO 1441. Et Cl H SO SO 1442. Et Cl H SO₂ SO1443. Et Cl H S SO₂ 1444. Et Cl H SO SO₂ 1445. Et Cl H SO₂ SO₂ 1446. EtCl H S NMe 1447. Et Cl H SO NMe 1448. Et Cl H SO₂ NMe

TABLE 5 Inventive compounds of the general formula (I) in which Q is Q2,R⁵ is hydrogen and n is 1

No. R¹ R³ R⁴ Y X 1H NMR 1449. Me Me Me S CH₂ 1450. Me Me Me SO CH₂ 1451.Me Me Me SO₂ CH₂ 1452. Me Me Me S CHMe 1453. Me Me Me SO CHMe 1454. MeMe Me SO₂ CHMe 1455. Me Me Me S C(CH₃)₂ 1456. Me Me Me SO C(CH₃)₂ 1457.Me Me Me SO₂ C(CH₃)₂ 1458. Me Me Me S C(OC₂H₄O) 1459. Me Me Me SOC(OC₂H₄O) 1460. Me Me Me SO₂ C(OC₂H₄O) 1461. Me Me Me S C(SC₂H₄S) 1462.Me Me Me SO C(SC₂H₄S) 1463. Me Me Me SO₂ C(SC₂H₄S) 1464. Me Me Me SCHOMe 1465. Me Me Me SO CHOMe 1466. Me Me Me SO₂ CHOMe 1467. Me Me Me SCHOEt 1468. Me Me Me SO CHOEt 1469. Me Me Me SO₂ CHOEt 1470. Me Me Me SCHOiPr 1471. Me Me Me SO CHOiPr 1472. Me Me Me SO₂ CHOiPr 1473. Me Me MeS CHOCH₂cPr 1474. Me Me Me SO CHOCH₂cPr 1475. Me Me Me SO₂ CHOCH₂cPr1476. Me Me Me S CHOC₂H₄OMe 1477. Me Me Me SO CHOC₂H₄OMe 1478. Me Me MeSO₂ CHOC₂H₄OMe 1479. Me Me Me S CHOCH₂CCH 1480. Me Me Me SO CHOCH₂CCH1481. Me Me Me SO₂ CHOCH₂CCH 1482. Me Me Me S CHOCH₂CH═CH₂ 1483. Me MeMe SO CHOCH₂CH═CH₂ 1484. Me Me Me SO₂ CHOCH₂CH═CH₂ 1485. Me Me Me S

1486. Me Me Me SO

1487. Me Me Me SO₂

1488. Me Me Me S

1489. Me Me Me SO

1490. Me Me Me SO₂

1491. Me Me Me S

1492. Me Me Me SO

1493. Me Me Me SO₂

1494. Me Me Me S

1495. Me Me Me SO

1496. Me Me Me SO₂

1497. Me Me Me S

1498. Me Me Me SO

1499. Me Me Me SO₂

1500. Me Me Me S CHOC₂H₄F 1501. Me Me Me SO CHOC₂H₄F 1502. Me Me Me SO₂CHOC₂H₄F 1503. Me Me Me S C═NOMe 1504. Me Me Me SO C═NOMe 1505. Me Me MeSO₂ C═NOMe 1506. Me Me Me S C═NOCH₂CCH 1507. Me Me Me SO C═NOCH₂CCH1508. Me Me Me SO₂ C═NOCH₂CCH 1509. Me Me Me S C═NOCH₂CH═CH₂ 1510. Me MeMe SO C═NOCH₂CH═CH₂ 1511. Me Me Me SO₂ C═NOCH₂CH═CH₂ 1512. Me Me Me SC═O 1513. Me Me Me SO C═O 1514. Me Me Me SO₂ C═O 1515. Me Me Me S C═S1516. Me Me Me SO C═S 1517. Me Me Me SO₂ C═S 1518. Me Me Me S C═S 1519.Me Me Me SO C═S 1520. Me Me Me SO₂ C═S 1521. Me Me Me S C═N—N(CH₃)₂1522. Me Me Me SO C═N—N(CH₃)₂ 1523. Me Me Me SO₂ C═N—N(CH₃)₂ 1524. Me MeMe S O 1525. Me Me Me SO O 1526. Me Me Me SO₂ O 1527. Me Me Me S S 1528.Me Me Me SO S 1529. Me Me Me SO₂ S 1530. Me Me Me S SO 1531. Me Me Me SOSO 1532. Me Me Me SO₂ SO 1533. Me Me Me S SO₂ 1534. Me Me Me SO SO₂1535. Me Me Me SO₂ SO₂ 1536. Me Me Me S NMe 1537. Me Me Me SO NMe 1538.Me Me Me SO₂ NMe 1539. Me Me Me O O 1540. Me Me H O O 1541. Me SMe H O O1542. Me Cl H O O 1543. Me Cl H S CH₂ 1544. Me Cl H SO CH₂ 1545. Me Cl HSO₂ CH₂ DMSO, 400 MHz: 3.40 (t, 2H), 3.74 (t, 2H), 3.79 (s, 3H), 7.89(br, 3H), 11.39 (s, 1H) 1546. Me Cl H S CHMe 1547. Me Cl H SO CHMe 1548.Me Cl H SO₂ CHMe 1549. Me Cl H S C(CH₃)₂ 1550. Me Cl H SO C(CH₃)₂ 1551.Me Cl H SO₂ C(CH₃)₂ 1552. Me Cl H S C(OC₂H₄O) 1553. Me Cl H SO C(OC₂H₄O)1554. Me Cl H SO₂ C(OC₂H₄O) 1555. Me Cl H S C(SC₂H₄S) 1556. Me Cl H SOC(SC₂H₄S) 1557. Me Cl H SO₂ C(SC₂H₄S) 1558. Me Cl H S CHOMe 1559. Me ClH SO CHOMe 1560. Me Cl H SO₂ CHOMe CDCl3, 400 MHz: 3.56 (s, 3H), 3.68(dd, 1H), 3.71 (d, 1H), 3.87 (s, 3H), 5.21 (d, 1H), 7.64 (s, 1H), 7.73(d, 1H), 7.91 (d, 1H), 9.85 (s, 1H) 1561. Me Cl H S CHOEt 1562. Me Cl HSO CHOEt 1563. Me Cl H SO₂ CHOEt 1564. Me Cl H S CHOiPr 1565. Me Cl H SOCHOiPr 1566. Me Cl H SO₂ CHOiPr 1567. Me Cl H S CHOCH₂cPr 1568. Me Cl HSO CHOCH₂cPr 1569. Me Cl H SO₂ CHOCH₂cPr 1570. Me Cl H S CHOC₂H₄OMe1571. Me Cl H SO CHOC₂H₄OMe 1572. Me Cl H SO₂ CHOC₂H₄OMe 1573. Me Cl H SCHOCH₂CCH 1574. Me Cl H SO CHOCH₂CCH 1575. Me Cl H SO₂ CHOCH₂CCH 1576.Me Cl H S CHOCH₂CH═CH₂ 1577. Me Cl H SO CHOCH₂CH═CH₂ 1578. Me Cl H SO₂CHOCH₂CH═CH₂ 1579. Me Cl H S

1580. Me Cl H SO

1581. Me Cl H SO₂

1582. Me Cl H S

1583. Me Cl H SO

1584. Me Cl H SO₂

1585. Me Cl H S

1586. Me Cl H SO

1587. Me Cl H SO₂

1588. Me Cl H S

1589. Me Cl H SO

1590. Me Cl H SO₂

1591. Me Cl H S

1592. Me Cl H SO

1593. Me Cl H SO₂

1594. Me Cl H S CHOC₂H₄F 1595. Me Cl H SO CHOC₂H₄F 1596. Me Cl H SO₂CHOC₂H₄F 1597. Me Cl H S C═NOMe 1598. Me Cl H SO C═NOMe 1599. Me Cl HSO₂ C═NOMe 1600. Me Cl H S C═NOCH₂CCH 1601. Me Cl H SO C═NOCH₂CCH 1602.Me Cl H SO₂ C═NOCH₂CCH 1603. Me Cl H S C═NOCH₂CH═CH₂ 1604. Me Cl H SOC═NOCH₂CH═CH₂ 1605. Me Cl H SO₂ C═NOCH₂CH═CH₂ 1606. Me Cl H S C═O 1607.Me Cl H SO C═O 1608. Me Cl H SO₂ C═O 1609. Me Cl H S C═S 1610. Me Cl HSO C═S 1611. Me Cl H SO₂ C═S 1612. Me Cl H S C═S 1613. Me Cl H SO C═S1614. Me Cl H SO₂ C═S 1615. Me Cl H S C═N—N(CH₃)₂ 1616. Me Cl H SOC═N—N(CH₃)₂ 1617. Me Cl H SO₂ C═N—N(CH₃)₂ 1618. Me Cl H S O 1619. Me ClH SO O 1620. Me Cl H SO₂ O 1621. Me Cl H S S 1622. Me Cl H SO S 1623. MeCl H SO₂ S 1624. Me Cl H S SO 1625. Me Cl H SO SO 1626. Me Cl H SO₂ SO1627. Me Cl H S SO₂ 1628. Me Cl H SO SO₂ 1629. Me Cl H SO₂ SO₂ 1630. MeCl H S NMe 1631. Me Cl H SO NMe 1632. Me Cl H SO₂ NMe 1633. Et Me Me SCH₂ 1634. Et Me Me SO CH₂ 1635. Et Me Me SO₂ CH₂ 1636. Et Me Me S CHMe1637. Et Me Me SO CHMe 1638. Et Me Me SO₂ CHMe 1639. Et Me Me S C(CH₃)₂1640. Et Me Me SO C(CH₃)₂ 1641. Et Me Me SO₂ C(CH₃)₂ 1642. Et Me Me SC(OC₂H₄O) 1643. Et Me Me SO C(OC₂H₄O) 1644. Et Me Me SO₂ C(OC₂H₄O) 1645.Et Me Me S C(SC₂H₄S) 1646. Et Me Me SO C(SC₂H₄S) 1647. Et Me Me SO₂C(SC₂H₄S) 1648. Et Me Me S CHOMe 1649. Et Me Me SO CHOMe 1650. Et Me MeSO₂ CHOMe 1651. Et Me Me S CHOEt 1652. Et Me Me SO CHOEt 1653. Et Me MeSO₂ CHOEt 1654. Et Me Me S CHOiPr 1655. Et Me Me SO CHOiPr 1656. Et MeMe SO₂ CHOiPr 1657. Et Me Me S CHOCH₂cPr 1658. Et Me Me SO CHOCH₂cPr1659. Et Me Me SO₂ CHOCH₂cPr 1660. Et Me Me S CHOC₂H₄OMe 1661. Et Me MeSO CHOC₂H₄OMe 1662. Et Me Me SO₂ CHOC₂H₄OMe 1663. Et Me Me S CHOCH₂CCH1664. Et Me Me SO CHOCH₂CCH 1665. Et Me Me SO₂ CHOCH₂CCH 1666. Et Me MeS CHOCH₂CH═CH₂ 1667. Et Me Me SO CHOCH₂CH═CH₂ 1668. Et Me Me SO₂CHOCH₂CH═CH₂ 1669. Et Me Me S

1670. Et Me Me SO

1671. Et Me Me SO₂

1672. Et Me Me S

1673. Et Me Me SO

1674. Et Me Me SO₂

1675. Et Me Me S

1676. Et Me Me SO

1677. Et Me Me SO₂

1678. Et Me Me S

1679. Et Me Me SO

1680. Et Me Me SO₂

1681. Et Me Me S

1682. Et Me Me SO

1683. Et Me Me SO₂

1684. Et Me Me S CHOC₂H₄F 1685. Et Me Me SO CHOC₂H₄F 1686. Et Me Me SO₂CHOC₂H₄F 1687. Et Me Me S C═NOMe 1688. Et Me Me SO C═NOMe 1689. Et Me MeSO₂ C═NOMe 1690. Et Me Me S C═NOCH₂CCH 1691. Et Me Me SO C═NOCH₂CCH1692. Et Me Me SO₂ C═NOCH₂CCH 1693. Et Me Me S C═NOCH₂CH═CH₂ 1694. Et MeMe SO C═NOCH₂CH═CH₂ 1695. Et Me Me SO₂ C═NOCH₂CH═CH₂ 1696. Et Me Me SC═O 1697. Et Me Me SO C═O 1698. Et Me Me SO₂ C═O 1699. Et Me Me S C═S1700. Et Me Me SO C═S 1701. Et Me Me SO₂ C═S 1702. Et Me Me S C═S 1703.Et Me Me SO C═S 1704. Et Me Me SO₂ C═S 1705. Et Me Me S C═N—N(CH₃)₂1706. Et Me Me SO C═N—N(CH₃)₂ 1707. Et Me Me SO₂ C═N—N(CH₃)₂ 1708. Et MeMe S O 1709. Et Me Me SO O 1710. Et Me Me SO₂ O 1711. Et Me Me S S 1712.Et Me Me SO S 1713. Et Me Me SO₂ S 1714. Et Me Me S SO 1715. Et Me Me SOSO 1716. Et Me Me SO₂ SO 1717. Et Me Me S SO₂ 1718. Et Me Me SO SO₂1719. Et Me Me SO₂ SO₂ 1720. Et Me Me S NMe 1721. Et Me Me SO NMe 1722.Et Me Me SO₂ NMe 1723. Et Me Me O O 1724. Et Me H O O 1725. Et SMe H O O1726. Et Cl H O O 1727. Et Cl H S CH₂ 1728. Et Cl H SO CH₂ 1729. Et Cl HSO₂ CH₂ 1730. Et Cl H S CHMe 1731. Et Cl H SO CHMe 1732. Et Cl H SO₂CHMe 1733. Et Cl H S C(CH₃)₂ 1734. Et Cl H SO C(CH₃)₂ 1735. Et Cl H SO₂C(CH₃)₂ 1736. Et Cl H S C(OC₂H₄O) 1737. Et Cl H SO C(OC₂H₄O) 1738. Et ClH SO₂ C(OC₂H₄O) 1739. Et Cl H S C(SC₂H₄S) 1740. Et Cl H SO C(SC₂H₄S)1741. Et Cl H SO₂ C(SC₂H₄S) 1742. Et Cl H S CHOMe 1743. Et Cl H SO CHOMe1744. Et Cl H SO₂ CHOMe 1745. Et Cl H S CHOEt 1746. Et Cl H SO CHOEt1747. Et Cl H SO₂ CHOEt 1748. Et Cl H S CHOiPr 1749. Et Cl H SO CHOiPr1750. Et Cl H SO₂ CHOiPr 1751. Et Cl H S CHOCH₂cPr 1752. Et Cl H SOCHOCH₂cPr 1753. Et Cl H SO₂ CHOCH₂cPr 1754. Et Cl H S CHOC₂H₄OMe 1755.Et Cl H SO CHOC₂H₄OMe 1756. Et Cl H SO₂ CHOC₂H₄OMe 1757. Et Cl H SCHOCH₂CCH 1758. Et Cl H SO CHOCH₂CCH 1759. Et Cl H SO₂ CHOCH₂CCH 1760.Et Cl H S CHOCH₂CH═CH₂ 1761. Et Cl H SO CHOCH₂CH═CH₂ 1762. Et Cl H SO₂CHOCH₂CH═CH₂ 1763. Et Cl H S

1764. Et Cl H SO

1765. Et Cl H SO₂

1766. Et Cl H S

1767. Et Cl H SO

1768. Et Cl H SO₂

1769. Et Cl H S

1770. Et Cl H SO

1771. Et Cl H SO₂

1772. Et Cl H S

1773. Et Cl H SO

1774. Et Cl H SO₂

1775. Et Cl H S

1776. Et Cl H SO

1777. Et Cl H SO₂

1778. Et Cl H S CHOC₂H₄F 1779. Et Cl H SO CHOC₂H₄F 1780. Et Cl H SO₂CHOC₂H₄F 1781. Et Cl H S C═NOMe 1782. Et Cl H SO C═NOMe 1783. Et Cl HSO₂ C═NOMe 1784. Et Cl H S C═NOCH₂CCH 1785. Et Cl H SO C═NOCH₂CCH 1786.Et Cl H SO₂ C═NOCH₂CCH 1787. Et Cl H S C═NOCH₂CH═CH₂ 1788. Et Cl H SOC═NOCH₂CH═CH₂ 1789. Et Cl H SO₂ C═NOCH₂CH═CH₂ 1790. Et Cl H S C═O 1791.Et Cl H SO C═O 1792. Et Cl H SO₂ C═O 1793. Et Cl H S C═S 1794. Et Cl HSO C═S 1795. Et Cl H SO₂ C═S 1796. Et Cl H S C═S 1797. Et Cl H SO C═S1798. Et Cl H SO₂ C═S 1799. Et Cl H S C═N—N (CH₃)₂ 1800. Et Cl H SOC═N—N (CH₃)₂ 1801. Et Cl H SO₂ C═N—N (CH₃)₂ 1802. Et Cl H S O 1803. EtCl H SO O 1804. Et Cl H SO₂ O 1805. Et Cl H S S 1806. Et Cl H SO S 1807.Et Cl H SO₂ S 1808. Et Cl H S SO 1809. Et Cl H SO SO 1810. Et Cl H SO₂SO 1811. Et Cl H S SO₂ 1812. Et Cl H SO SO₂ 1813. Et Cl H SO₂ SO₂ 1814.Et Cl H S NMe 1815. Et Cl H SO NMe 1816. Et Cl H SO₂ NMe

TABLE 6 Inventive compounds of the general formula (I) in which Q is Q3,R⁵ is hydrogen and n is 1

No. R² R³ R⁴ Y X 1H NMR 1817. Me Me Me S CH₂ 1818. Me Me Me SO CH₂ 1819.Me Me Me SO₂ CH₂ 1820. Me Me Me S CHMe 1821. Me Me Me SO CHMe 1822. MeMe Me SO₂ CHMe 1823. Me Me Me S C(CH₃)₂ 1824. Me Me Me SO C(CH₃)₂ 1825.Me Me Me SO₂ C(CH₃)₂ 1826. Me Me Me S C(OC₂H₄O) 1827. Me Me Me SOC(OC₂H₄O) 1828. Me Me Me SO₂ C(OC₂H₄O) 1829. Me Me Me S C(SC₂H₄S) 1830.Me Me Me SO C(SC₂H₄S) 1831. Me Me Me SO₂ C(SC₂H₄S) 1832. Me Me Me SCHOMe 1833. Me Me Me SO CHOMe 1834. Me Me Me SO₂ CHOMe 1835. Me Me Me SCHOEt 1836. Me Me Me SO CHOEt 1837. Me Me Me SO₂ CHOEt 1838. Me Me Me SCHOiPr 1839. Me Me Me SO CHOiPr 1840. Me Me Me SO₂ CHOiPr 1841. Me Me MeS CHOCH₂cPr 1842. Me Me Me SO CHOCH₂cPr 1843. Me Me Me SO₂ CHOCH₂cPr1844. Me Me Me S CHOC₂H₄OMe 1845. Me Me Me SO CHOC₂H₄OMe 1846. Me Me MeSO₂ CHOC₂H₄OMe 1847. Me Me Me S CHOCH₂CCH 1848. Me Me Me SO CHOCH₂CCH1849. Me Me Me SO₂ CHOCH₂CCH 1850. Me Me Me S CHOCH₂CH═CH₂ 1851. Me MeMe SO CHOCH₂CH═CH₂ 1852. Me Me Me SO₂ CHOCH₂CH═CH₂ 1853. Me Me Me S

1854. Me Me Me SO

1855. Me Me Me SO₂

1856. Me Me Me S

1857. Me Me Me SO

1858. Me Me Me SO₂

1859. Me Me Me S

1860. Me Me Me SO

1861. Me Me Me SO₂

1862. Me Me Me S

1863. Me Me Me SO

1864. Me Me Me SO₂

1865. Me Me Me S

1866. Me Me Me SO

1867. Me Me Me SO₂

1868. Me Me Me S CHOC₂H₄F 1869. Me Me Me SO CHOC₂H₄F 1870. Me Me Me SO₂CHOC₂H₄F 1871. Me Me Me S C═NOMe 1872. Me Me Me SO C═NOMe 1873. Me Me MeSO₂ C═NOMe 1874. Me Me Me S C═NOCH₂CCH 1875. Me Me Me SO C═NOCH₂CCH1876. Me Me Me SO₂ C═NOCH₂CCH 1877. Me Me Me S C═NOCH₂CH═CH₂ 1878. Me MeMe SO C═NOCH₂CH═CH₂ 1879. Me Me Me SO₂ C═NOCH₂CH═CH₂ 1880. Me Me Me SC═O 1881. Me Me Me SO C═O 1882. Me Me Me SO₂ C═O 1883. Me Me Me S C═S1884. Me Me Me SO C═S 1885. Me Me Me SO₂ C═S 1886. Me Me Me S C═S 1887.Me Me Me SO C═S 1888. Me Me Me SO₂ C═S 1889. Me Me Me S C═N—N(CH₃)₂1890. Me Me Me SO C═N—N(CH₃)₂ 1891. Me Me Me SO₂ C═N—N(CH₃)₂ 1892. Me MeMe S O 1893. Me Me Me SO O 1894. Me Me Me SO₂ O 1895. Me Me Me S S 1896.Me Me Me SO S 1897. Me Me Me SO₂ S 1898. Me Me Me S SO 1899. Me Me Me SOSO 1900. Me Me Me SO₂ SO 1901. Me Me Me S SO₂ 1902. Me Me Me SO SO₂1903. Me Me Me SO₂ SO₂ 1904. Me Me Me S NMe 1905. Me Me Me SO NMe 1906.Me Me Me SO₂ NMe 1907. Me Me Me O O 1908. Me Me H O O 1909. Me SMe H O O1910. Me Cl H O O 1911. Me Cl H S CH₂ 1912. Me Cl H SO CH₂ 1913. Me Cl HSO₂ CH₂ CDCl3, 400 MHz: 2.52 (s, 3H), 3.47 (t, 2H), 3.62 (t, 2H), 3.79(s, 3H), 7.80 (d, 1H), 7.88 (d, 1H), 8.14 (s, 1H) 1914. Me Cl H S CHMe1915. Me Cl H SO CHMe 1916. Me Cl H SO₂ CHMe 1917. Me Cl H S C(CH₃)₂1918. Me Cl H SO C(CH₃)₂ 1919. Me Cl H SO₂ C(CH₃)₂ 1920. Me Cl H SC(OC₂H₄O) 1921. Me Cl H SO C(OC₂H₄O) 1922. Me Cl H SO₂ C(OC₂H₄O) 1923.Me Cl H S C(SC₂H₄S) 1924. Me Cl H SO C(SC₂H₄S) 1925. Me Cl H SO₂C(SC₂H₄S) 1926. Me Cl H S CHOMe 1927. Me Cl H SO CHOMe 1928. Me Cl H SO₂CHOMe CDCl3, 400 MHz: 2.44 (s, 3H), 3.53 (s, 3H), 3.57 (dd, 1H), 3.71(d, 1H), 5.15 (d, 1H), 7.55 (d, 1H), 7.74 (d, 1H), 9.40 (s, 1H) 1929. MeCl H S CHOEt 1930. Me Cl H SO CHOEt 1931. Me Cl H SO₂ CHOEt 1932. Me ClH S CHOiPr 1933. Me Cl H SO CHOiPr 1934. Me Cl H SO₂ CHOiPr 1935. Me ClH S CHOCH₂cPr 1936. Me Cl H SO CHOCH₂cPr 1937. Me Cl H SO₂ CHOCH₂cPr1938. Me Cl H S CHOC₂H₄OMe 1939. Me Cl H SO CHOC₂H₄OMe 1940. Me Cl H SO₂CHOC₂H₄OMe 1941. Me Cl H S CHOCH₂CCH 1942. Me Cl H SO CHOCH₂CCH 1943. MeCl H SO₂ CHOCH₂CCH 1944. Me Cl H S CHOCH₂CH═CH₂ 1945. Me Cl H SOCHOCH₂CH═CH₂ 1946. Me Cl H SO₂ CHOCH₂CH═CH₂ 1947. Me Cl H S

1948. Me Cl H SO

1949. Me Cl H SO₂

1950. Me Cl H S

1951. Me Cl H SO

1952. Me Cl H SO₂

1953. Me Cl H S

1954. Me Cl H SO

1955. Me Cl H SO₂

1956. Me Cl H S

1957. Me Cl H SO

1958. Me Cl H SO₂

1959. Me Cl H S

1960. Me Cl H SO

1961. Me Cl H SO₂

1962. Me Cl H S CHOC₂H₄F 1963. Me Cl H SO CHOC₂H₄F 1964. Me Cl H SO₂CHOC₂H₄F 1965. Me Cl H S C═NOMe 1966. Me Cl H SO C═NOMe 1967. Me Cl HSO₂ C═NOMe 1968. Me Cl H S C═NOCH₂CCH 1969. Me Cl H SO C═NOCH₂CCH 1970.Me Cl H SO₂ C═NOCH₂CCH 1971. Me Cl H S C═NOCH₂CH═CH₂ 1972. Me Cl H SOC═NOCH₂CH═CH₂ 1973. Me Cl H SO₂ C═NOCH₂CH═CH₂ 1974. Me Cl H S C═O 1975.Me Cl H SO C═O 1976. Me Cl H SO₂ C═O 1977. Me Cl H S C═S 1978. Me Cl HSO C═S 1979. Me Cl H SO₂ C═S 1980. Me Cl H S C═S 1981. Me Cl H SO C═S1982. Me Cl H SO₂ C═S 1983. Me Cl H S C═N—N(CH₃)₂ 1984. Me Cl H SOC═N—N(CH₃)₂ 1985. Me Cl H SO₂ C═N—N(CH₃)₂ 1986. Me Cl H S O 1987. Me ClH SO O 1988. Me Cl H SO₂ O 1989. Me Cl H S S 1990. Me Cl H SO S 1991. MeCl H SO₂ S 1992. Me Cl H S SO 1993. Me Cl H SO SO 1994. Me Cl H SO₂ SO1995. Me Cl H S SO₂ 1996. Me Cl H SO SO₂ 1997. Me Cl H SO₂ SO₂ 1998. MeCl H S NMe 1999. Me Cl H SO NMe 2000. Me Cl H SO₂ NMe 2001. Et Me Me SCH₂ 2002. Et Me Me SO CH₂ 2003. Et Me Me SO₂ CH₂ 2004. Et Me Me S CHMe2005. Et Me Me SO CHMe 2006. Et Me Me SO₂ CHMe 2007. Et Me Me S C(CH₃)₂2008. Et Me Me SO C(CH₃)₂ 2009. Et Me Me SO₂ C(CH₃)₂ 2010. Et Me Me SC(OC₂H₄O) 2011. Et Me Me SO C(OC₂H₄O) 2012. Et Me Me SO₂ C(OC₂H₄O) 2013.Et Me Me S C(SC₂H₄S) 2014. Et Me Me SO C(SC₂H₄S) 2015. Et Me Me SO₂C(SC₂H₄S) 2016. Et Me Me S CHOMe 2017. Et Me Me SO CHOMe 2018. Et Me MeSO₂ CHOMe 2019. Et Me Me S CHOEt 2020. Et Me Me SO CHOEt 2021. Et Me MeSO₂ CHOEt 2022. Et Me Me S CHOiPr 2023. Et Me Me SO CHOiPr 2024. Et MeMe SO₂ CHOiPr 2025. Et Me Me S CHOCH₂cPr 2026. Et Me Me SO CHOCH₂cPr2027. Et Me Me SO₂ CHOCH₂cPr 2028. Et Me Me S CHOC₂H₄OMe 2029. Et Me MeSO CHOC₂H₄OMe 2030. Et Me Me SO₂ CHOC₂H₄OMe 2031. Et Me Me S CHOCH₂CCH2032. Et Me Me SO CHOCH₂CCH 2033. Et Me Me SO₂ CHOCH₂CCH 2034. Et Me MeS CHOCH₂CH═CH₂ 2035. Et Me Me SO CHOCH₂CH═CH₂ 2036. Et Me Me SO₂CHOCH₂CH═CH₂ 2037. Et Me Me S

2038. Et Me Me SO

2039. Et Me Me SO₂

2040. Et Me Me S

2041. Et Me Me SO

2042. Et Me Me SO₂

2043. Et Me Me S

2044. Et Me Me SO

2045. Et Me Me SO₂

2046. Et Me Me S

2047. Et Me Me SO

2048. Et Me Me SO₂

2049. Et Me Me S

2050. Et Me Me SO

2051. Et Me Me SO₂

2052. Et Me Me S CHOC₂H₄F 2053. Et Me Me SO CHOC₂H₄F 2054. Et Me Me SO₂CHOC₂H₄F 2055. Et Me Me S C═NOMe 2056. Et Me Me SO C═NOMe 2057. Et Me MeSO₂ C═NOMe 2058. Et Me Me S C═NOCH₂CCH 2059. Et Me Me SO C═NOCH₂CCH2060. Et Me Me SO₂ C═NOCH₂CCH 2061. Et Me Me S C═NOCH₂CH═CH₂ 2062. Et MeMe SO C═NOCH₂CH═CH₂ 2063. Et Me Me SO₂ C═NOCH₂CH═CH₂ 2064. Et Me Me SC═O 2065. Et Me Me SO C═O 2066. Et Me Me SO₂ C═O 2067. Et Me Me S C═S2068. Et Me Me SO C═S 2069. Et Me Me SO₂ C═S 2070. Et Me Me S C═S 2071.Et Me Me SO C═S 2072. Et Me Me SO₂ C═S 2073. Et Me Me S C═N—N(CH₃)₂2074. Et Me Me SO C═N—N(CH₃)₂ 2075. Et Me Me SO₂ C═N—N(CH₃)₂ 2076. Et MeMe S O 2077. Et Me Me SO O 2078. Et Me Me SO₂ O 2079. Et Me Me S S 2080.Et Me Me SO S 2081. Et Me Me SO₂ S 2082. Et Me Me S SO 2083. Et Me Me SOSO 2084. Et Me Me SO₂ SO 2085. Et Me Me S SO₂ 2086. Et Me Me SO SO₂2087. Et Me Me SO₂ SO₂ 2088. Et Me Me S NMe 2089. Et Me Me SO NMe 2090.Et Me Me SO₂ NMe 2091. Et Me Me O O 2092. Et Me H O O 2093. Et SMe H O O2094. Et Cl H O O 2095. Et Cl H S CH₂ 2096. Et Cl H SO CH₂ 2097. Et Cl HSO₂ CH₂ 2098. Et Cl H S CHMe 2099. Et Cl H SO CHMe 2100. Et Cl H SO₂CHMe 2101. Et Cl H S C(CH₃)₂ 2102. Et Cl H SO C(CH₃)₂ 2103. Et Cl H SO₂C(CH₃)₂ 2104. Et Cl H S C(OC₂H₄O) 2105. Et Cl H SO C(OC₂H₄O) 2106. Et ClH SO₂ C(OC₂H₄O) 2107. Et Cl H S C(SC₂H₄S) 2108. Et Cl H SO C(SC₂H₄S)2109. Et Cl H SO₂ C(SC₂H₄S) 2110. Et Cl H S CHOMe 2111. Et Cl H SO CHOMe2112. Et Cl H SO₂ CHOMe 2113. Et Cl H S CHOEt 2114. Et Cl H SO CHOEt2115. Et Cl H SO₂ CHOEt 2116. Et Cl H S CHOiPr 2117. Et Cl H SO CHOiPr2118. Et Cl H SO₂ CHOiPr 2119. Et Cl H S CHOCH₂cPr 2120. Et Cl H SOCHOCH₂cPr 2121. Et Cl H SO₂ CHOCH₂cPr 2122. Et Cl H S CHOC₂H₄OMe 2123.Et Cl H SO CHOC₂H₄OMe 2124. Et Cl H SO₂ CHOC₂H₄OMe 2125. Et Cl H SCHOCH₂CCH 2126. Et Cl H SO CHOCH₂CCH 2127. Et Cl H SO₂ CHOCH₂CCH 2128.Et Cl H S CHOCH₂CH═CH₂ 2129. Et Cl H SO CHOCH₂CH═CH₂ 2130. Et Cl H SO₂CHOCH₂CH═CH₂ 2131. Et Cl H S

2132. Et Cl H SO

2133. Et Cl H SO₂

2134. Et Cl H S

2135. Et Cl H SO

2136. Et Cl H SO₂

2137. Et Cl H S

2138. Et Cl H SO

2139. Et Cl H SO₂

2140. Et Cl H S

2141. Et Cl H SO

2142. Et Cl H SO₂

2143. Et Cl H S

2144. Et Cl H SO

2145. Et Cl H SO₂

2146. Et Cl H S CHOC₂H₄F 2147. Et Cl H SO CHOC₂H₄F 2148. Et Cl H SO₂CHOC₂H₄F 2149. Et Cl H S C═NOMe 2150. Et Cl H SO C═NOMe 2151. Et Cl HSO₂ C═NOMe 2152. Et Cl H S C═NOCH₂CCH 2153. Et Cl H SO C═NOCH₂CCH 2154.Et Cl H SO₂ C═NOCH₂CCH 2155. Et Cl H S C═NOCH₂CH═CH₂ 2156. Et Cl H SOC═NOCH₂CH═CH₂ 2157. Et Cl H SO₂ C═NOCH₂CH═CH₂ 2158. Et Cl H S C═O 2159.Et Cl H SO C═O 2160. Et Cl H SO₂ C═O 2161. Et Cl H S C═S 2162. Et Cl HSO C═S 2163. Et Cl H SO₂ C═S 2164. Et Cl H S C═S 2165. Et Cl H SO C═S2166. Et Cl H SO₂ C═S 2167. Et Cl H S C═N—N(CH₃)₂ 2168. Et Cl H SOC═N—N(CH₃)₂ 2169. Et Cl H SO₂ C═N—N(CH₃)₂ 2170. Et Cl H S O 2171. Et ClH SO O 2172. Et Cl H SO₂ O 2173. Et Cl H S S 2174. Et Cl H SO S 2175. EtCl H SO₂ S 2176. Et Cl H S SO 2177. Et Cl H SO SO 2178. Et Cl H SO₂ SO2179. Et Cl H S SO₂ 2180. Et Cl H SO SO₂ 2181. Et Cl H SO₂ SO₂ 2182. EtCl H S NMe 2183. Et Cl H SO NMe 2184. Et Cl H SO₂ NMe

TABLE 7 Inventive compounds of the general formula (I) in which Q is Q1,X and Y are each oxygen, R⁵ is fluorine and n is 1

No. R¹ R³ R⁴ 1H NMR 2185. Me Me Me 2186. Me Me H DMSO-d6, 400 MHz: 7.62(d, 1H), 7.40 (d, 1H), 3.90 (s, 3H), 2.39 (s, 3H) 2187. Me Cl H 2188. MeSMe H 2189. Me Me Me 2190. Me Me H 2191. Me Cl H 2192. Me SMe H 2193. EtMe Me 2194. Et Me H 2195. Et Cl H 2196. Et SMe H 2197. Et Me Me 2198. EtMe H 2199. Et Cl H 2200. Et SMe H

TABLE 8 Inventive compounds of the general formula (I) in which Q is Q3,X is 2-(1,4-pyrazinyl)oxymethyl, Y is SO₂, R⁵ is hydrogen and n is 2

No. R² R³ R⁴ 1H NMR 2201. Cl Me Me 2202. Cl Me H 2203. Cl Cl H 2204. OMeMe Me DMSO-d₆, 400 MHz: 11.36 (s, 1H), 8.38 (s, 1H), 8.33-8.31 (m, 2H),7.60 (s, 1H), 6.51 (dd, 1H), 4.07 (s, 3H), 3.77-3.70 (m, 1H), 3.58-3.53(m, 1H), 2.76-2.60 (m, 5H), 2.18 (s, 3H) 2205. OMe Me H 2206. OMe Cl H2207. NHAc Me Me 2208. NHAc Me H 2209. NHAc Cl H

TABLE 9 Inventive compounds of the general formula (I) in which Q is Q1,Y is SO₂, R⁵ is hydrogen and n is 1

No. R¹ R³ R⁴ X 1H NMR 2210. nPr Me Me CH₂ 2211. nPr Me H CH₂ 2212. nPrCl H CH₂ DMSO-d₆, 400 MHz: 0.89 (t, 3H), 1.89 (m, 2H), 3.42 (t, 2H),3.76 (t, 2H), 4.33 (t, 2H), 7.90 (d, 1H), 7.94 (d, 1H), 11.84 (s, 1H)2213. C₂H₄OMe Me Me CH₂ 2214. C₂H₄OMe Me H CH₂ 2215. C₂H₄OMe Cl H CH₂2216. CH₂CF₃ Me Me CH₂ 2217. CH₂CF₃ Me H CH₂ 2218. CH₂CF₃ Cl H CH₂ 2219.nPr Me Me CHOMe 2220. nPr Me H CHOMe 2221. nPr Cl H CHOMe DMSO-d₆, 400MHz: 0.99 (t, 3H), 2.01 (m, 2H), 3.53 (s, 3H), 3.63 (dd, 1H), 3.80 (d,1H), 4.40 (t, 2H), 5.22 (d, 1H), 7.72 (d, 1H), 7.92 (d, 1H), 10.80 (s,1H) 2222. C₂H₄OMe Me Me CHOMe 2223. C₂H₄OMe Me H CHOMe 2224. C₂H₄OMe ClH CHOMe 2225. CH₂CF₃ Me Me CHOMe 2226. CH₂CF₃ Me H CHOMe 2227. CH₂CF₃ ClH CHOMe

TABLE 10 Inventive compounds of the general formula (I) in which Q is Q1and R⁵ is hydrogen and n is 1

No. R¹ R³ R⁴ X Y 1H NMR 2228. Me Me Me S C═O 2229. Me Me Me SO C═O 2230.Me Me Me SO₂ C═O 2231. Me Me Me S CHOMe 2232. Me Me Me SO CHOMe 2233. MeMe Me SO₂ CHOMe 2234. Me Me Me S CHOEt 2235. Me Me Me SO CHOEt 2236. MeMe Me SO₂ CHOEt 2237. Me Me Me S C═NOMe 2238. Me Me Me SO C═NOMe 2239.Me Me Me SO₂ C═NOMe 2240. Me Me Me S C═NOEt 2241. Me Me Me SO C═NOEt2242. Me Me Me SO₂ C═NOEt 2243. Me Me Me S O 2244. Me Me Me SO O 2245.Me Me Me SO₂ O 2246. Me Me Me S S 2247. Me Me Me SO S 2248. Me Me Me SO₂S 2249. Me Me Me S SO₂ 2250. Me Me Me SO SO₂ 2251. Me Me Me SO₂ SO₂2252. Me Me H S C═O 2253. Me Me H SO C═O 2254. Me Me H SO₂ C═O 2255. MeMe H S CHOMe 2256. Me Me H SO CHOMe 2257. Me Me H SO₂ CHOMe 2258. Me MeH S CHOEt 2259. Me Me H SO CHOEt 2260. Me Me H SO₂ CHOEt 2261. Me Me H SC═NOMe 2262. Me Me H SO C═NOMe 2263. Me Me H SO₂ C═NOMe 2264. Me Me H SC═NOEt 2265. Me Me H SO C═NOEt 2266. Me Me H SO₂ C═NOEt 2267. Me Me H SO 2268. Me Me H SO O 2269. Me Me H SO₂ O 2270. Me Me H S S 2271. Me Me HSO S 2272. Me Me H SO₂ S 2273. Me Me H S SO₂ 2274. Me Me H SO SO₂ 2275.Me Me H SO₂ SO₂

TABLE 11 Inventive compounds of the general formula (I) in which Q isQ2, R⁵ is hydrogen and n is 1

No. R¹ R³ R⁴ X Y 1H NMR 2276. Me Me Me S C═O 2277. Me Me Me SO C═O 2278.Me Me Me SO₂ C═O 2279. Me Me Me S CHOMe 2280. Me Me Me SO CHOMe 2281. MeMe Me SO₂ CHOMe 2282. Me Me Me S CHOEt 2283. Me Me Me SO CHOEt 2284. MeMe Me SO₂ CHOEt 2285. Me Me Me S C═NOMe 2286. Me Me Me SO C═NOMe 2287.Me Me Me SO₂ C═NOMe 2288. Me Me Me S C═NOEt 2289. Me Me Me SO C═NOEt2290. Me Me Me SO₂ C═NOEt 2291. Me Me Me S O 2292. Me Me Me SO O 2293.Me Me Me SO₂ O 2294. Me Me Me S S 2295. Me Me Me SO S 2296. Me Me Me SO₂S 2297. Me Me Me S SO₂ 2298. Me Me Me SO SO₂ 2299. Me Me Me SO₂ SO₂2300. Me Me H S C═O 2301. Me Me H SO C═O 2302. Me Me H SO₂ C═O 2303. MeMe H S CHOMe 2304. Me Me H SO CHOMe 2305. Me Me H SO₂ CHOMe 2306. Me MeH S CHOEt 2307. Me Me H SO CHOEt 2308. Me Me H SO₂ CHOEt 2309. Me Me H SC═NOMe 2310. Me Me H SO C═NOMe 2311. Me Me H SO₂ C═NOMe 2312. Me Me H SC═NOEt 2313. Me Me H SO C═NOEt 2314. Me Me H SO₂ C═NOEt 2315. Me Me H SO 2316. Me Me H SO O 2317. Me Me H SO₂ O 2318. Me Me H S S 2319. Me Me HSO S 2320. Me Me H SO₂ S 2321. Me Me H S SO₂ 2322. Me Me H SO SO₂ 2323.Me Me H SO₂ SO₂

TABLE 12 Inventive compounds of the general formula (I) in which Q isQ3, R⁵ is hydrogen and n is 1

No. R² R³ R⁴ X Y 1H NMR 2324. Me Me Me S C═O 2325. Me Me Me SO C═O 2326.Me Me Me SO₂ C═O 2327. Me Me Me S CHOMe 2328. Me Me Me SO CHOMe 2329. MeMe Me SO₂ CHOMe 2330. Me Me Me S CHOEt 2331. Me Me Me SO CHOEt 2332. MeMe Me SO₂ CHOEt 2333. Me Me Me S C═NOMe 2334. Me Me Me SO C═NOMe 2335.Me Me Me SO₂ C═NOMe 2336. Me Me Me S C═NOEt 2337. Me Me Me SO C═NOEt2338. Me Me Me SO₂ C═NOEt 2339. Me Me Me S O 2340. Me Me Me SO O 2341.Me Me Me SO₂ O 2342. Me Me Me S S 2343. Me Me Me SO S 2344. Me Me Me SO₂S 2345. Me Me Me S SO₂ 2346. Me Me Me SO SO₂ 2347. Me Me Me SO₂ SO₂2348. Me Me H S C═O 2349. Me Me H SO C═O 2350. Me Me H SO₂ C═O 2351. MeMe H S CHOMe 2352. Me Me H SO CHOMe 2353. Me Me H SO₂ CHOMe 2354. Me MeH S CHOEt 2355. Me Me H SO CHOEt 2356. Me Me H SO₂ CHOEt 2357. Me Me H SC═NOMe 2358. Me Me H SO C═NOMe 2359. Me Me H SO₂ C═NOMe 2360. Me Me H SC═NOEt 2361. Me Me H SO C═NOEt 2362. Me Me H SO₂ C═NOEt 2363. Me Me H SO 2364. Me Me H SO O 2365. Me Me H SO₂ O 2366. Me Me H S S 2367. Me Me HSO S 2368. Me Me H SO₂ S 2369. Me Me H S SO₂ 2370. Me Me H SO SO₂ 2371.Me Me H SO₂ SO₂

TABLE 13 Inventive compounds of the general formula (I) in which Q isQ1, R⁵ is hydrogen and n is 2

No. R¹ R³ R⁴ X Y 1H NMR 2372. Me Me Me S C═O 2373. Me Me Me SO C═O 2374.Me Me Me SO₂ C═O 2375. Me Me Me S CHOMe 2376. Me Me Me SO CHOMe 2377. MeMe Me SO₂ CHOMe 2378. Me Me Me S CHOEt 2379. Me Me Me SO CHOEt 2380. MeMe Me SO₂ CHOEt 2381. Me Me Me S C═NOMe 2382. Me Me Me SO C═NOMe 2383.Me Me Me SO₂ C═NOMe 2384. Me Me Me S C═NOEt 2385. Me Me Me SO C═NOEt2386. Me Me Me SO₂ C═NOEt 2387. Me Me Me S O 2388. Me Me Me SO O 2389.Me Me Me SO₂ O 2390. Me Me Me S S 2391. Me Me Me SO S 2392. Me Me Me SO₂S 2393. Me Me Me S SO₂ 2394. Me Me Me SO SO₂ 2395. Me Me Me SO₂ SO₂2396. Me Me H S C═O 2397. Me Me H SO C═O 2398. Me Me H SO₂ C═O 2399. MeMe H S CHOMe 2400. Me Me H SO CHOMe 2401. Me Me H SO₂ CHOMe 2402. Me MeH S CHOEt 2403. Me Me H SO CHOEt 2404. Me Me H SO₂ CHOEt 2405. Me Me H SC═NOMe 2406. Me Me H SO C═NOMe 2407. Me Me H SO₂ C═NOMe 2408. Me Me H SC═NOEt 2409. Me Me H SO C═NOEt 2410. Me Me H SO₂ C═NOEt 2411. Me Me H SO 2412. Me Me H SO O 2413. Me Me H SO₂ O 2414. Me Me H S S 2415. Me Me HSO S 2416. Me Me H SO₂ S 2417. Me Me H S SO₂ 2418. Me Me H SO SO₂ 2419.Me Me H SO₂ SO₂

TABLE 14 Inventive compounds of the general formula (I) in which Q isQ2, R⁵ is hydrogen and n is 2

No. R¹ R³ R⁴ X Y 1H NMR 2420. Me Me Me S C═O 2421. Me Me Me SO C═O 2422.Me Me Me SO₂ C═O 2423. Me Me Me S CHOMe 2424. Me Me Me SO CHOMe 2425. MeMe Me SO₂ CHOMe 2426. Me Me Me S CHOEt 2427. Me Me Me SO CHOEt 2428. MeMe Me SO₂ CHOEt 2429. Me Me Me S C═NOMe 2430. Me Me Me SO C═NOMe 2431.Me Me Me SO₂ C═NOMe 2432. Me Me Me S C═NOEt 2433. Me Me Me SO C═NOEt2434. Me Me Me SO₂ C═NOEt 2435. Me Me Me S O 2436. Me Me Me SO O 2437.Me Me Me SO₂ O 2438. Me Me Me S S 2439. Me Me Me SO S 2440. Me Me Me SO₂S 2441. Me Me Me S SO₂ 2442. Me Me Me SO SO₂ 2443. Me Me Me SO₂ SO₂2444. Me Me H S C═O 2445. Me Me H SO C═O 2446. Me Me H SO₂ C═O 2447. MeMe H S CHOMe 2448. Me Me H SO CHOMe 2449. Me Me H SO₂ CHOMe 2450. Me MeH S CHOEt 2451. Me Me H SO CHOEt 2452. Me Me H SO₂ CHOEt 2453. Me Me H SC═NOMe 2454. Me Me H SO C═NOMe 2455. Me Me H SO₂ C═NOMe 2456. Me Me H SC═NOEt 2457. Me Me H SO C═NOEt 2458. Me Me H SO₂ C═NOEt 2459. Me Me H SO 2460. Me Me H SO O 2461. Me Me H SO₂ O 2462. Me Me H S S 2463. Me Me HSO S 2464. Me Me H SO₂ S 2465. Me Me H S SO₂ 2466. Me Me H SO SO₂ 2467.Me Me H SO₂ SO₂

TABLE 15 Inventive compounds of the general formula (I) in which Q isQ3, R⁵ is hydrogen and n is 2

No. R¹ R³ R⁴ X Y 1H NMR 2468. Me Me Me S C═O 2469. Me Me Me SO C═O 2470.Me Me Me SO₂ C═O 2471. Me Me Me S CHOMe 2472. Me Me Me SO CHOMe 2473. MeMe Me SO₂ CHOMe 2474. Me Me Me S CHOEt 2475. Me Me Me SO CHOEt 2476. MeMe Me SO₂ CHOEt 2477. Me Me Me S C═NOMe 2478. Me Me Me SO C═NOMe 2479.Me Me Me SO₂ C═NOMe 2480. Me Me Me S C═NOEt 2481. Me Me Me SO C═NOEt2482. Me Me Me SO₂ C═NOEt 2483. Me Me Me S O 2484. Me Me Me SO O 2485.Me Me Me SO₂ O 2486. Me Me Me S S 2487. Me Me Me SO S 2488. Me Me Me SO₂S 2489. Me Me Me S SO₂ 2490. Me Me Me SO SO₂ 2491. Me Me Me SO₂ SO₂2492. Me Me H S C═O 2493. Me Me H SO C═O 2494. Me Me H SO₂ C═O 2495. MeMe H S CHOMe 2496. Me Me H SO CHOMe 2497. Me Me H SO₂ CHOMe 2498. Me MeH S CHOEt 2499. Me Me H SO CHOEt 2500. Me Me H SO₂ CHOEt 2501. Me Me H SC═NOMe 2502. Me Me H SO C═NOMe 2503. Me Me H SO₂ C═NOMe 2504. Me Me H SC═NOEt 2505. Me Me H SO C═NOEt 2506. Me Me H SO₂ C═NOEt 2507. Me Me H SO 2508. Me Me H SO O 2509. Me Me H SO₂ O 2510. Me Me H S S 2511. Me Me HSO S 2512. Me Me H SO₂ S 2513. Me Me H S SO₂ 2514. Me Me H SO SO₂ 2515.Me Me H SO₂ SO₂

B. FORMULATION EXAMPLES

-   a) A dusting product is obtained by mixing 10 parts by weight of a    compound of the formula (I) and/or a salt thereof and 90 parts by    weight of talc as an inert substance, and comminuting the mixture in    a hammer mill.-   b) A readily water-dispersible wettable powder is obtained by mixing    25 parts by weight of a compound of the formula (I) and/or salts    thereof, 64 parts by weight of kaolin-containing quartz as an inert    substance, 10 parts by weight of potassium lignosulfonate and 1 part    by weight of sodium oleylmethyltaurate as a wetting agent and    dispersant, and grinding the mixture in a pinned-disk mill.-   c) A readily water-dispersible dispersion concentrate is obtained by    mixing 20 parts by weight of a compound of the formula (I) and/or    salts thereof with 6 parts by weight of alkylphenol polyglycol ether    (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether    (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling    range for example about 255 to above 277° C.), and grinding the    mixture in a ball mill to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I) and/or salts thereof, 75 parts by    weight of cyclohexanone as a solvent and 10 parts by weight of    ethoxylated nonylphenol as an emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium laurylsulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin,    -   grinding the mixture in a pinned-disk mill and granulating the        powder in a fluidized bed by spraying on water as a granulating        liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting    -   25 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate,    -   2 parts by weight of sodium oleylmethyltaurate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water    -   in a colloid mill, then grinding the mixture in a bead mill and        atomizing and drying the resulting suspension in a spray tower        by means of a one-substance nozzle.

C. BIOLOGICAL EXAMPLES 1. Pre-Emergence Herbicidal Action AgainstHarmful Plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare placed in wood-fiber pots in sandy loam and covered with soil. Theinventive compounds formulated in the form of wettable powders (WP) oras emulsion concentrates (EC) are then applied to the surface of thecovering soil as an aqueous suspension or emulsion at a waterapplication rate of 600 to 800 l/ha (converted) with addition of 0.2%wetting agent. After the treatment, the pots are placed in a greenhouseand kept under good growth conditions for the test plants. The damage tothe test plants is assessed visually after a test period of 3 weeks bycomparison with untreated controls (herbicidal activity in percent (%):100% action=the plants have died, 0% action=like control plants). Forexample, compounds No. 7, 9, 40, 187 and 189 at an application rate of320 g/ha each show at least 80% efficacy against Abutilon theophrastiand Amaranthus retroflexus. Compounds No. 9, 40, 187, 189 and 2204 at anapplication rate of 320 g/ha each show at least 80% efficacy againstMatricaria inodora, Stellaria media and Veronica persica.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants areplaced in sandy loam in wood-fiber pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants are treated at the one-leaf stage. Theinventive compounds formulated in the form of wettable powders (WP) oras emulsion concentrates (EC) are then sprayed onto the green parts ofthe plants as an aqueous suspension or emulsion at a water applicationrate of 600 to 800 l/ha (converted) with addition of 0.2% wetting agent.After the test plants have been left to stand in the greenhouse underoptimal growth conditions for about 3 weeks, the action of theformulations is scored visually in comparison to untreated controls(herbicidal action in percent (%): 100% action=the plants have died, 0%action=like control plants).

Examples of good post-emergence efficacy (PO). For example, compoundsNo. 7 and 2204 at an application rate of 80 g/ha each show at least 80%efficacy against Abutilon theophrasti and Viola tricolor. Compounds No.9, 187 and 189 at an application rate of 80 g/ha each show at least 80%efficacy against Abutilon theophrasti and Amaranthus retroflexus.Compounds No. 40, 187 and 189 at an application rate of 80 g/ha eachshow at least 80% efficacy against Matricaria inodora, Stellaria mediaand Veronica Persica.

The invention claimed is:
 1. An N-(1,2,5-oxadiazol-3-yl)-,N-(tetrazol-5-yl)- or N-(triazol-5-yl)bicycloarylcarboxamide of theformula (I) or a salt thereof

in which Q is a Q1, Q2 or Q3 radical,

R¹ is (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₂-C₆)-alkynyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁ ⁻C₆)⁻alkoxy-(C₂-C₆)-alkenyl, (C₁-C₆)-alkoxy-(C₂-C₆)-alkynyl, CH₂R⁶,heteroaryl, heterocyclyl or phenyl, where the three latter radicals areeach substituted by u radicals from the group consisting of halogen,nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,(C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl; R²is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl,(C₂-C₆)-alkenyloxy, halo-(C₂-C₆)-alkenyl, (C₂ ₋C₆)-alkynyl,(C₂-C₆)-alkynyloxy, halo-(C₂-C₆)-alkynyl, cyano, nitro, methylsulfenyl,methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino,methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl,trifluoromethylcarbonyl, halogen, amino, aminocarbonyl,methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, orheteroaryl, heterocyclyl or phenyl each substituted by u radicalsselected from the group consisting of methyl, ethyl, methoxy,trifluoromethyl and halogen; R³ and R⁴ are each independently hydrogen,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₇)-cycloalkyl, (C₃-C₇)-halocycloalkyl, (C₁-C₆)-alkoxy,(C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio,(C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl,(C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitroor cyano; R⁵ is hydrogen or fluorine; R⁶ is acetoxy, acetamido,N-methylacetamido, benzoyloxy, benzamido, N-methylbenz-amido,methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl,piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl,aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl,(C₃-C₆)-cycloalkyl, or heteroaryl, heterocyclyl or phenyl eachsubstituted by u radicals selected from the group consisting of methyl,ethyl, methoxy, trifluoromethyl and halogen; R⁷ and R⁸ are eachindependently hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl, halo-(C₃-C₇) -cycloalkyl,-OR⁹, S(O)_(m)R⁹, (C₁-C₆)-alkylthio, halo-(C₁-C₆)-alkylthio,(C₁-C₆)-alkylsulfinyl, halo-(C₁-C₆)-alkylsulfinyl,(C₁-C₆)-alkylsulfonyl, halo-(C₁-C₆)-alkyl-sulfonyl,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro, cyano, heteroaryl,heterocyclyl or phenyl, where the three latter radicals are eachsubstituted by u radicals selected from the group consisting of halogen,nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,(C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁⁻C₆)⁻ alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, orR⁷ and R⁸ together with the carbon atom to which they are bonded form a—X¹—(CH₂)_(r)—X²—, —(CH₂)_(s)—X³—, —(CH₂)_(t)—X³—CH₂—,—(CH₂)_(v)—X³—CH₂CH₂— or —(CH₂)_(w)— unit in which each of the (CH₂)groups is substituted by m radicals selected from the group consistingof halogen, methyl and (C₁-C₃)-alkoxy, or R⁷ and R⁸ together with thecarbon atom to which they are bonded form the—O—N((C₁-C₃)-alkyl)-CHR¹⁰—CH₂— or —O—N═CR¹⁰—CH₂— unit in which each ofthe (CH₂) groups is substituted by m radicals selected from the groupconsisting of halogen and methyl; R⁹ is hydrogen, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl,(C₃-C₇)-halocycloalkyl, (C₃-C₇)-cycloalkyl-(C₁-C₃)-alkyl,halo-(C₃-C₇)-cycloalkyl-(C₁-C₃)-alkyl, heteroaryl, heterocyclyl orphenyl, where the three latter radicals are each substituted by sradicals selected from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆) -alkyl, (C₃-C₆)-cycloalkyl,(C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl;R¹⁰ is hydrogen, (C₁-C₃)-alkyl, or phenyl substituted by u radicalsselected from the group Consisting of (C₁-C₃)-alkyl, halogen, cyano andnitro; R¹¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,formyl, (C₂-C₆)-alkylcarbonyl, (C₂-C₆)-alkoxycarbonyl or(C₁-C₂)-alkylsulfonyl; X and Y are independently O, S, SO, SO₂, C═O,C═S, NR¹⁰, CR⁷R⁸, C═NOR¹⁰ or C═NN(R¹¹)₂; X¹ and X² are eachindependently O, S or N((C₁-C₃)-alkyl); X³ is O or S; m is 0, 1 or 2; nis 2; r is 2, 3 or 4; s is 2, 3, 4 or 5; t is 1, 2, 3 or 4; u is 0, 1, 2or 3; v is 2 or 3; and w is 2, 3, 4, 5 or
 6. 2. AnN-(1,2,5-oxadiazol-3-yl)—, N-(tetrazol-5-yl)- orN-(triazol-5-yl)bicycloarylcarboxamide as claimed in claim 1, in whichR¹ is (C₁-C₃)-alkyl, (C₃-C₅)-cycloalkyl, halo-(C₁-C₃)-alkyl or(C₁-C₃)-alkoxy-(C₁-C₃)-alkyl; R² is hydrogen, (C₁-C₃)-alkyl,(C₃-C₅)-cycloalkyl, halo-(C₁-C₃)-alkyl, (C₁-C₃)-alkoxy,halo-(C₁-C₃)-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl,methylsulfonyl, acetylamino, methoxycarbonyl, ethoxycarbonyl, halogen,amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl ormethoxymethyl; R³ and R⁴ are each independently hydrogen, (C₁-C₃)-alkyl,halo-(C₁-C₃)-alkyl, (C₃ ^(-C) ₅)-cycloalkyl, (C₁-C₃)-alkoxy,(C₁-C₃)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl,(C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro orcyano; R⁵ is hydrogen; R⁷ and R⁸ are each independently hydrogen,(C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃ ^(-C) ₅)-cycloalkyl, —OR⁹,—S(O)_(m)R⁹, (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl,(C₁-C₃)-alkylsulfonyl, (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl, halogen, nitro,cyano, heteroaryl, heterocyclyl or phenyl, where the three latterradicals are each substituted by u radicals selected from the groupconsisting of halogen, nitro, cyano, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl,(C₃-C₅)-cycloalkyl, (C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl,(C₁-C₃)-alkylsulfonyl, (C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy and(C₁-C₃)-alkoxy-(C₁-C₃)-alkyl, or R⁷ and R⁸ together with the carbon atomto which they are bonded form a —X¹—(CH₂),—X²—, —(CH₂)_(s),—X³—,—(CH₂)_(t)—X³—CH₂—, —(CH₂)_(v)—X³—CH₂CH₂— or —(CH₂)_(w)— unit in whicheach of the (CH₂) groups is substituted by m radicals selected from thegroup consisting of halogen, methyl and (C₁-C₃)-alkoxy, or R⁷ and R⁸together with the carbon atom to which they are bonded form the—O—N((C₁-C₃)-alkyl)-CHR¹⁰—CH₂— or —O—N═CR¹⁰—CH₂— unit in which each ofthe (CH₂) groups is substituted by m radicals selected from the groupconsisting of halogen and methyl; R⁹ is hydrogen, (C₁-C₃)-alkyl,halo-(C₁-C₃)-alkyl, (C₂-C₃)-alkenyl, (C₂-C₄)-alkynyl,(C₃-C₅)-cycloalkyl, (C₃-C₅)-cycloalkyl-(C₁-C₃)-alkyl, heteroaryl,heterocyclyl or phenyl, where the three latter radicals are eachsubstituted by s radicals selected from the group consisting of halogen,nitro, cyano, (C₁-C₃)-alkyl, halo-(C₁-C₃)-alkyl, (C₃-C₆)-cycloalkyl,(C₁-C₃)-alkylthio, (C₁-C₃)-alkylsulfinyl, (C₁-C₃)-alkylsulfonyl,(C₁-C₃)-alkoxy, halo-(C₁-C₃)-alkoxy and (C₁-C₃)-alkoxy-(C₁-C₃)-alkyl;R¹⁰ is hydrogen or (C₁-C₃)-alkyl; X and Y are each independently O, SO₂,C═O, C═S, CR⁷R⁸, C═NOR¹⁰; X¹ and X² are each independently O, S, N(CH₃);X³ is O or S; m is 0, 1 or 2; n is 2; r is2or3; s is 2, 3 or 4; t is 1,2 or 3; u is 0, 1 or 2; v is 2 or 3; and w is2,3,4or5.
 3. A herbicidalcomposition, comprising a herbicidally active content of at least onecompound of the formula (I) as claimed in claim
 1. 4. The herbicidalcomposition as claimed in claim 3, in a mixture with at least oneformulation auxiliary.
 5. A herbicidal composition as claimed in claim 3additionally comprising at least one pesticidally active substanceselected from the group consisting of an insecticide, an acaricide, afurther herbicide, a fungicide, a safener and a growth regulator.
 6. Theherbicidal composition as claimed in claim 5, comprising a safener.
 7. Aherbicidal composition as claimed in claim 6, comprising cyprosulfamide,cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
 8. Aherbicidal composition as claimed in claim 5, comprising a furtherherbicide.
 9. The compound of formula (I) and/or a salt thereof asclaimed in claim 1 capable of being used for controlling an unwantedplant.
 10. The compound of formula (I) and/or a salt thereof as claimedin claim 1, wherein said compound of formula (I) is capable of beingused for controlling an unwanted plant in a crop of a useful plant. 11.The compound of formula (I) capable of being used as claimed in claim10, wherein said useful plant is a transgenic useful plant.
 12. Thecompound of formula (I) and/or a salt thereof as claimed in claim 2,capable of being used for controlling an unwanted plant.
 13. Aherbicidal composition as claimed in claim 3 capable of being used forcontrolling an unwanted plant.
 14. AnN-(tetrazol-5-yl)bicycloarylcarboxamide as claimed in claim 1 having theformula


15. An N-(tetrazol-5-yl)bicycloarylcarboxamide as claimed in claim 1having the formula


16. An N-(tetrazol-5-yl)bicycloarylcarboxamide as claimed in claim 1having the formula


17. An N-(tetrazol-5-yl)bicycloarylcarboxamide as claimed in claim 1having the formula


18. An N-(tetrazol-5-yl)bicycloarylcarboxamide as claimed in claim 1having the formula